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

HRID 1977356Notes

Reaction equation

HRID 1977356 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.[CH2:18]([O:20][C:21]([C:23]1[S:24][C:25]([C:28](Cl)=[O:29])=[CH:26][CH:27]=1)=[O:22])[CH3:19]>C(#N)C>[CH2:18]([O:20][C:21]([C:23]1[S:24][C:25]([C:28](=[O:29])[NH:6][CH2:5][C:4]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:2]([Cl:1])[CH:3]=2)=[CH:26][CH:27]=1)=[O:22])[CH3:19]

Participants

5

Reactant 3

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 8471TriethylamineHCID 102628585-Carboethoxythiophen-2-carbonyl chloride

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-c05bbf029e834921973d197aa13b86b8
Source dataset
uspto-grants-2001_05
Patent number
US06232338B1

Reaction notes

Loading…