1-(2-(Aminocarbothioyl)carbohydrazonoyl)-4-methyl-5-isoquinolinyl acetate

Base Information

• Chemical Name: 1-(2-(Aminocarbothioyl)carbohydrazonoyl)-4-methyl-5-isoquinolinyl acetate
• CAS No.: 171880-39-0
• Molecular Formula: C₁₄H₁₄N₄O₂S
• Molecular Weight: 302.357
• NSC Number: 687304
• ChEMBL ID: CHEMBL1985160
• Mol file: 171880-39-0.mol

Synonyms:NSC687304;NSC 687304;171880-39-0;1-(2-(Aminocarbothioyl)carbohydrazonoyl)-4-methyl-5-isoquinolinyl acetate;CHEMBL1985160;NSC-687304;[1-[(E)-(carbamothioylhydrazono)methyl]-4-methyl-5-isoquinolyl] acetate;Hydrazinecarbothioamide, 2-[[4-(acetyloxy)-5-methyl- 1-isoquinolinyl]methylene]-

Chemical Property of 1-(2-(Aminocarbothioyl)carbohydrazonoyl)-4-methyl-5-isoquinolinyl acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 517.486°C at 760 mmHg
• Flash Point: 266.766°C
• Density: 1.358g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 302.08374688
• Heavy Atom Count: 21
• Complexity: 429

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C2=C1C(=CC=C2)OC(=O)C)C=NNC(=S)N
• Isomeric SMILES: CC1=CN=C(C2=C1C(=CC=C2)OC(=O)C)/C=N/NC(=S)N

Technology Process of 1-(2-(Aminocarbothioyl)carbohydrazonoyl)-4-methyl-5-isoquinolinyl acetate

There total 9 articles about 1-(2-(Aminocarbothioyl)carbohydrazonoyl)-4-methyl-5-isoquinolinyl acetate 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:

1,5-dimethylisoquinoline (72678-15-0) → 4-acetoxy-5-methylisoquinoline-1-carboxaldehyde thiosemicarbazone (171880-39-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / 30percent aq. H₂O₂, glacial AcOH / 30 h / 65 - 70 °C

2: 1.) AcOH, AcONa, 2.) 10percent aq. HCl / 1.) from 80 deg C to 85 deg C, 2 h, 2.) reflux, 1 h

3: 86 percent / pyridine / 0 - 20 °C

4: 49 percent / SeO₂ / dioxane / 3 h / Heating

5: aq. HCl / ethanol / Heating

With pyridine; hydrogenchloride; selenium(IV) oxide; dihydrogen peroxide; sodium acetate; acetic acid; In 1,4-dioxane; ethanol;

DOI:10.1021/jm00021a012

Reference yield:

1,5-dimethyl-3,4-dihydroisoquinoline (41566-63-6) → 4-acetoxy-5-methylisoquinoline-1-carboxaldehyde thiosemicarbazone (171880-39-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / phenyl disulfide / 1,2,3,4-tetrahydro-naphthalene / 15 h / 200 - 205 °C

2: 86 percent / 30percent aq. H₂O₂, glacial AcOH / 30 h / 65 - 70 °C

3: 1.) AcOH, AcONa, 2.) 10percent aq. HCl / 1.) from 80 deg C to 85 deg C, 2 h, 2.) reflux, 1 h

4: 86 percent / pyridine / 0 - 20 °C

5: 49 percent / SeO₂ / dioxane / 3 h / Heating

6: aq. HCl / ethanol / Heating

With pyridine; hydrogenchloride; selenium(IV) oxide; dihydrogen peroxide; sodium acetate; acetic acid; diphenyldisulfane; In 1,4-dioxane; tetralin; ethanol;

DOI:10.1021/jm00021a012

Reference yield:

2-methylphenethylamine (55755-16-3) → 4-acetoxy-5-methylisoquinoline-1-carboxaldehyde thiosemicarbazone (171880-39-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / pyridine / 0 - 20 °C

2: 99 percent / poly(phosphoric acid) / 4 h / 160 - 165 °C

3: 94 percent / phenyl disulfide / 1,2,3,4-tetrahydro-naphthalene / 15 h / 200 - 205 °C

4: 86 percent / 30percent aq. H₂O₂, glacial AcOH / 30 h / 65 - 70 °C

5: 1.) AcOH, AcONa, 2.) 10percent aq. HCl / 1.) from 80 deg C to 85 deg C, 2 h, 2.) reflux, 1 h

6: 86 percent / pyridine / 0 - 20 °C

7: 49 percent / SeO₂ / dioxane / 3 h / Heating

8: aq. HCl / ethanol / Heating

With pyridine; hydrogenchloride; selenium(IV) oxide; poly(phosphoric acid); dihydrogen peroxide; sodium acetate; acetic acid; diphenyldisulfane; In 1,4-dioxane; tetralin; ethanol;

DOI:10.1021/jm00021a012

upstream raw materials:

thiosemicarbazide

4-acetoxy-5-methylisoquinoline-1-carboxaldehyde

1,5-dimethylisoquinoline

1,5-dimethyl-3,4-dihydroisoquinoline