Benzenemethanamine, 3,4-dichloro- → 5-(3,4-Dichlorobenzyl-carbamoyl)-thiophene-2-carboxylic acid ethyl ester

HRID 1263609Notes

Reaction equation

HRID 1263609 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH2:6].C(N(CC)CC)C.C(OC(N1C[C@@H](S)C[C@H]1CN[C:32]([C:34]1[S:35][C:36]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:37][CH:38]=1)=[O:33])=O)C=C>C(#N)C>[CH2:42]([O:41][C:39]([C:36]1[S:35][C:34]([C:32](=[O:33])[NH:6][CH2:5][C:4]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:2]([Cl:1])[CH:3]=2)=[CH:38][CH:37]=1)=[O:40])[CH3:43]

Participants

5

Reactant 3

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 8471TriethylamineHCID 59048576(2S,4S)2-{[(5-ethoxycarbonyl-thiophene-2-carbonyl)-amino]-methyl}-4-sulfanyl-pyrrolidine-1-carboxylic acid allyl ester

Product 1

HCID 229861535-(3,4-Dichlorobenzyl-carbamoyl)-thiophene-2-carboxylic acid ethyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Starting material (12(e)) was prepared as follows. To a stirring solution of 3,4-dichlorobenzylamine (0.53 mL; 4.0 mmole) in acetonitrile (10 mL) was added triethylamine (1.67 mL; 12.0 mmole) and a solution of (11(a)) (0.87 g; 4.0 mmole. see Example 11) in acetonitrile (20 mL). The solution was stirred at ambient temperature, under argon, for 22 hours. The solvent and excess triethylamine were removed in vacuo and the residue partitioned between chloroform and water. The organic phase was washed with water and brine, dried over magnesium sulphate and vacuumed to dryness to give 5-(3,4-dichlorobenzyl-carbamoyl)-thiophene-2-carboxylic acid ethyl ester (12(a)) as a cream solid (90%).

Workup

  1. customwas prepared
  2. customThe solvent and excess triethylamine were removed in vacuo
  3. customthe residue partitioned between chloroform and water
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-233b6bd6d7d24f37b57c1a2bc5433d88
Source dataset
uspto-grants-2003_04
Patent number
US06541491B1

Reaction notes

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