5-(aminosulfonyl)-3-chloro-1-methyl-1H- pyrazol

Base Information

• Chemical Name: 5-(aminosulfonyl)-3-chloro-1-methyl-1H- pyrazol
• CAS No.: 100784-27-8
• Molecular Formula: C6H8ClN3O4S
• Molecular Weight: 253.66
• Hs Code.: 2935009090
• DSSTox Substance ID: DTXSID60442169
• Nikkaji Number: J829.502F
• Wikidata: Q72442064
• Mol file: 100784-27-8.mol

Synonyms:3-Chloro-1-methyl-5-sulfamoyl-1H-pyrazole-4-carboxylicacid methyl ester;5-(Aminosulfonyl)-3-chloro-1-methyl-1H-pyrazole-4-carboxylic acid methyl ester;

Chemical Property of 5-(aminosulfonyl)-3-chloro-1-methyl-1H- pyrazol

Chemical Property:

• Melting Point: 138-139℃
• Refractive Index: 无资料
• Boiling Point: 473.406 °C at 760 mmHg
• PKA: 9.22±0.60(Predicted)
• Flash Point: 240.108 °C
• PSA: 86.36000
• Density: 1.753 g/cm³
• LogP: 1.50200
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 252.9924046
• Heavy Atom Count: 15
• Complexity: 354

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-Chloro-1-methyl-5-sulfamoyl-1H-pyrazole-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=C(C(=N1)Cl)C(=O)OC)S(=O)(=O)N
• Uses: Methyl 3-Chloro-1-methyl-5-sulfamoyl-1H-pyrazole-4-carboxylic Acid is used as a reactant in the synthesis of Halosulfuron Methyl (H104053), a herbicide. Methyl 3-Chloro-1-methyl-5-sulfamoyl-1H-pyrazole-4-carboxylic Acid is also a hydrolysis product of Halosulfuron Methyl.

Technology Process of 5-(aminosulfonyl)-3-chloro-1-methyl-1H- pyrazol

There total 11 articles about 5-(aminosulfonyl)-3-chloro-1-methyl-1H- pyrazol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.1%

methyl 3-chloro-5-(chlorosulfonyl)-1-methyl-1H-pyrazole-4-carboxylate → 3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide (100784-27-8)

Guidance literature:

With ammonium hydroxide; at 50 ℃; for 2h;

Reference yield:

methyl ester of 1-methylpyrazole-4-carboxylic acid (5952-93-2) → 3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide (100784-27-8)

Guidance literature:

Multi-step reaction with 4 steps

1: N-chlorosuccinimide / 120 °C

2: 73 percent / N-chlorosuccinimide / 160 °C

3: 96 percent / 70percent sodium hydrosulfide / dimethylformamide / 0.5 h / 60 °C

4: 1.) chlorine, aq. AcOH, 2.) 28percent aq. NH₃ / 1.) 5 deg C, 2.) 1,2-dichloroethane, RT, 0.5 h

With ammonium hydroxide; N-chloro-succinimide; sodium hydrogensulfide; chlorine; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570340231

Reference yield:

methyl 3-amino-1-methylpyrazole-4-carboxylate (64182-19-0) → 3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide (100784-27-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 35percent aq. HCl, sodium nitrite, 2.) cuprous chloride, 35percent aq. HCl / 1.) 0 deg C, 1 h, 2.) CHCl₃, RT, 1 h

2: N-chlorosuccinimide / 120 °C

3: 73 percent / N-chlorosuccinimide / 160 °C

4: 96 percent / 70percent sodium hydrosulfide / dimethylformamide / 0.5 h / 60 °C

5: 1.) chlorine, aq. AcOH, 2.) 28percent aq. NH₃ / 1.) 5 deg C, 2.) 1,2-dichloroethane, RT, 0.5 h

With hydrogenchloride; ammonium hydroxide; N-chloro-succinimide; sodium hydrogensulfide; chlorine; acetic acid; copper(l) chloride; sodium nitrite; In N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570340231

upstream raw materials:

methyl 3-chloro-5-mercapto-1-methyl-1H-pyrazole-4-carboxylate

Methyl 5-Chloro-1-methylpyrazole-4-carboxylate

methyl ester of 1-methylpyrazole-4-carboxylic acid

methyl 3-amino-1-methylpyrazole-4-carboxylate

Downstream raw materials:

halosulfuron methyl

Refernces

• 1、 -. "Halosulfuron methyl intermediate synthesis method". . . Retrieved 2017/10/07.
• 2、 Morimoto, Katsushi,Sato, Toshiaki,Yamamoto, Susumu,Takeuchi, Hiroshi. "Synthesis of Halosulfuron-methyl via Selective Chlorination at 3- and/or 5-Position of Pyrazole-4-carboxylates". . p. 537 - 540. Retrieved 2007/10/03.