Hydroxyhexamide

Base Information

• Chemical Name: Hydroxyhexamide
• CAS No.: 3168-01-2
• Molecular Formula: C15H22 N2 O4 S
• Molecular Weight: 326.417
• Hs Code.: 2935009090
• UNII: F3F26TZ9HN
• DSSTox Substance ID: DTXSID50953633
• Nikkaji Number: J9.524I
• Wikidata: Q27277583
• ChEMBL ID: CHEMBL2105052
• Mol file: 3168-01-2.mol

Synonyms:hydroxyhexamide;hydroxyhexamide, (+-)-isomer;hydroxyhexamide, (S)-isomer

Chemical Property of Hydroxyhexamide

Chemical Property:

• Vapor Pressure: 2.37E-11mmHg at 25°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 107.37000
• Density: 1.31g/cm³
• LogP: 3.73660
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 326.13002836
• Heavy Atom Count: 22
• Complexity: 460

Purity/Quality:

99.3% ^*data from raw suppliers

Hydroxyhexamide >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC2CCCCC2)O

Technology Process of Hydroxyhexamide

There total 8 articles about Hydroxyhexamide 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: 90.0%

(+/-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (220948-18-5) → (+/-)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (3168-01-2)

Guidance literature:

With methanol; potassium carbonate; for 12h; Ambient temperature;

DOI:10.1016/S0957-4166(98)00436-4

Reference yield:

acetohexamide (968-81-0) → (+/-)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (3168-01-2)

Guidance literature:

in vitro reduction in the presence of NADPH or NADH; effects of various inhibitors on reducing activity;

DOI:10.1248/cpb.33.3548

Reference yield:

4-acetylbenzenesulfonamide (1565-17-9) → (+/-)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (3168-01-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / NaBH₄ / methanol / 0.5 h / 0 °C

2: 87 percent / pyridine / 2 h / -10 °C

3: 1.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) benzene, RT, 30 min, 2.) benzene, RT, 1 h

4: 90 percent / K₂CO₃, MeOH / 12 h / Ambient temperature

With pyridine; methanol; sodium tetrahydroborate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol;

DOI:10.1016/S0957-4166(98)00436-4

upstream raw materials:

acetohexamide

(+/-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide

p-ethylbenzenesulfonyl chloride

4-acetylbenzenesulfonamide

Downstream raw materials:

(R)-(+)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide

Refernces

• 1、 Akita, Hiroyuki,Kurashima, Katsumi,Nozawa, Masako,Yamamura, Shigeo,Seri, Kenzi,Imamura, Yorishige. "Determination of absolute configuration of a metabolite (-)- hydroxyhexamide from acetohexamide, syntheses of (-)- and (+)- hydroxyhexamides and (-)- and (+)-acetoxyhexamides". . p. 4331 - 4340. Retrieved 2007/10/03.