methyl 6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carboxylate

Base Information

• Chemical Name: methyl 6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carboxylate
• CAS No.: 118783-07-6
• Molecular Formula: C₂₃H₂₁ClN₆O₇S₂
• Molecular Weight: 593.041
• Mol file: 118783-07-6.mol

Synonyms:methyl 6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carboxylate

Chemical Property of methyl 6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carboxylate

There total 6 articles about methyl 6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carboxylate 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%

methyl 6<ethyl>amino>methyl>-4-chloropyridine-2-carboxylate (118783-06-5) + 2-nitrobenzenesulfenyl chloride (7669-54-7) → methyl 6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carboxylate (118783-07-6)

Guidance literature:

With triethylamine; trifluoroacetic acid; In dichloromethane; 0 deg C, 30 min, then RT, 6 h;

DOI:10.1016/S0040-4020(88)90018-X

Reference yield:

dimethyl 4-chloro-2,6-pyridinedicarboxylate (5371-70-0) → methyl 6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carboxylate (118783-07-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / NaBH₄ / methanol / 0 deg C to RT, 3 h

2: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO, CH₂Cl₂, -30 deg C, 20 min, 2.) -60 deg C, 25 min, then RT

3: molecular sieve 3A / acetonitrile / 12 h / Ambient temperature

4: NaBH₄ / methanol / 0 deg C, then RT, 20 min

5: 90 percent / trifluoroacetic acid, Et₃N / CH₂Cl₂ / 0 deg C, 30 min, then RT, 6 h

With sodium tetrahydroborate; oxalyl dichloride; 3 A molecular sieve; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(88)90018-X

Reference yield:

methyl 4-chloro-6-hydroxymethylpyridine-2-carboxylate (109880-43-5) → methyl 6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carboxylate (118783-07-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO, CH₂Cl₂, -30 deg C, 20 min, 2.) -60 deg C, 25 min, then RT

2: molecular sieve 3A / acetonitrile / 12 h / Ambient temperature

3: NaBH₄ / methanol / 0 deg C, then RT, 20 min

4: 90 percent / trifluoroacetic acid, Et₃N / CH₂Cl₂ / 0 deg C, 30 min, then RT, 6 h

With sodium tetrahydroborate; oxalyl dichloride; 3 A molecular sieve; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(88)90018-X

upstream raw materials:

methyl 6<ethyl>amino>methyl>-4-chloropyridine-2-carboxylate

2-nitrobenzenesulfenyl chloride

dimethyl 4-chloro-2,6-pyridinedicarboxylate

methyl 4-chloro-6-hydroxymethylpyridine-2-carboxylate

Downstream raw materials:

6-{[[(S)-2-Carbamoyl-2-(2-nitro-phenylsulfanylamino)-ethyl]-(2-nitro-phenylsulfanyl)-amino]-methyl}-4-chloro-pyridine-2-carboxylic acid

N^α-<6-<ethyl>-N-(o-nitrophenylthio)amino>methyl>-4-chloropyridine-2-carbonyl>-erithro-β-tert-butoxy-L-histidine tert-butyl ester