Ethyl bromoacetate → HCID 178468148, compound

HRID 1194339Notes

Reaction equation

HRID 1194339 reaction equation
[Na].[CH2:2]([C:9]1[CH:18]=[CH:17][C:12]2[NH:13][C:14](=[S:16])[NH:15][C:11]=2[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:19]([O:21][C:22](=O)[CH2:23]Br)[CH3:20]>C(O)C>[CH2:19]([O:21][C:22](=[SH:16][C:14]1[NH:15][C:11]2[CH:10]=[C:9]([CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:18]=[CH:17][C:12]=2[N:13]=1)[CH3:23])[CH3:20]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 5360545SodiumHCID 21269540HCID 21269540, compound

Product 1

HCID 178468148HCID 178468148, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.46 g (20 mmoles) of metal sodium are dissolved in 40 ml of ethanol. To the ethylate 4.8 g (20 mmoles) of 5-benzyl-benzimidazoline-2-thione are added and 2.4 ml of bromoacetic acid ethyl ester are added dropwise at room temperature. After 4 hours boiling the salt is filtered off, the mother liquor is evaporated and 60 ml of petrol-ether are added to the distillation residue. Thus 7.23 g of crude title product are isolated. This is purified by suspending in water. Thus 6.33 g (97.1%) of title compound melting at a temperature of 103° C. are obtained, which can be crystallized from methanol.

Workup

  1. filtrationthe salt is filtered off
  2. customthe mother liquor is evaporated
  3. addition60 ml of petrol-ether are added to the distillation residue
  4. customThus 7.23 g of crude title product are isolated
  5. customThis is purified

Sources & evidence

ORD record
ord-15b7b629b4854c578d8ad0771ac3cebd
Source dataset
uspto-grants-1989_03
Patent number
US04814329

Reaction notes

Loading…