Cyclohexanone → Methyl 4-{3-[(benzo[1,3]dioxol-5-ylmethyl)carbamoyl]-4,5,6,7-tetrahydrobenzo[b]thiophene-2-ylcarbamoyl}benzoate

HRID 1856839Notes

Reaction equation

HRID 1856839 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1C(Cl)=O)=[O:4].[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([CH2:23][NH:24][C:25]([C:27]3[C:28]4[CH2:36][CH2:35][CH2:34][CH2:33][C:29]=4[S:30][C:31]=3[NH2:32])=[O:26])=[CH:22][C:17]=2[O:16][CH2:15]1.[C:37]1(=[O:43])CCCCC1.O1C2C=CC(CNC(=O)CC#N)=CC=2OC1.[S]>ClCCl.N1C=CC=CC=1>[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([CH2:23][NH:24][C:25]([C:27]3[C:28]4[CH2:36][CH2:35][CH2:34][CH2:33][C:29]=4[S:30][C:31]=3[NH:32][C:37]([C:11]3[CH:10]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:13][CH:12]=3)=[O:43])=[O:26])=[CH:22][C:17]=2[O:16][CH2:15]1

Participants

8

Reactant 5

HCID 7967CyclohexanoneHCID 4342112N-(1,3-benzodioxol-5-ylmethyl)-2-cyanoacetamideHCID 5362487SulfurHCID 11159939Methyl 2-(carbonochloridoyl)benzoateHCID 11782481N-(benzo[1,3]dioxol-5-ylmethyl)-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

Product 1

HCID 10907136Methyl 4-{3-[(benzo[1,3]dioxol-5-ylmethyl)carbamoyl]-4,5,6,7-tetrahydrobenzo[b]thiophene-2-ylcarbamoyl}benzoate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

1.0 g of methoxycarbonylbenzoyl chloride ("A") is added to a solution of 1.5 g of N-(benzo[1,3]dioxol-5-ylmethyl)-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide [obtainable by reacting cyclohexanone with N-benzo[1,3]dioxol-5-ylmethyl-2-cyanoacetamide in the presence of sulphur) in 50 ml of dichloromethane and 2 ml of pyridine and stirring is carried out for 2 hours at room temperature. The solvent is removed and is worked up in the customary manner. 1.3 g of methyl 4-{3-[(benzo[1,3]dioxol-5-ylmethyl)carbamoyl]-4,5,6,7-tetrahydrobenzo[b]thiophene-2-ylcarbamoyl}benzoate, m.p. 165°, are obtained.

Workup

  1. customThe solvent is removed

Sources & evidence

ORD record
ord-c6a02c14fc9f4efc94de6e2540a8c7c2
Source dataset
uspto-grants-2000_11
Patent number
US06143777

Reaction notes

Loading…