Sodium hydride → Methyl 3-(4-chlorobenzoylamino)-3-(3-thienylcarbonyl)propionate

HRID 1462428Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][C:10]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)=[O:11])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH:9]([C:10]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)=[O:11])[CH2:22][C:23]([O:25][CH3:26])=[O:24])=[O:7])=[CH:17][CH:18]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 60984Methyl bromoacetate

HCID 13105428N-(4-chlorobenzoyl)-N-[(3-thienylcarbonyl)methyl]amine

Product 1

HCID 13345231Methyl 3-(4-chlorobenzoylamino)-3-(3-thienylcarbonyl)propionateYield 64.3%

Procedure

23 g of N-(4-chlorobenzoyl)-N-[(3-thienylcarbonyl)methyl]amine, 6.1 g of 50% sodium hydride and 21.8 g of methyl bromoacetate are treated in the same manner as described in Preparation 1-(4). 18.6 g of methyl 3-(4-chlorobenzoylamino)-3-(3-thienylcarbonyl)propionate are thereby obtained.

Workup

customas described in Preparation 1-(4)

Sources & evidence

ORD record: ord-3cb2f8f29aaa4bcc83289eda39117c6a
Source dataset: uspto-grants-1984_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04460596

Reaction notes

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