Ethyl chloroacetate → HCID 54345847, compound

HRID 1940208Notes

Reaction equation

HRID 1940208 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]([CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:7](=[O:19])[CH2:8][C:9](=[O:18])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.[CH2:27]([O:29][C:30](=[O:33])[CH2:31]Cl)[CH3:28].[H-].[Na+]>CN(C)C=O>[CH2:27]([O:29][C:30](=[O:33])[CH2:31][CH:8]1[C:7](=[O:19])[N:6]([CH2:20][C:21]([CH3:23])([CH3:22])[CH3:24])[C:5]2[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][C:4]=2[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:9]1=[O:18])[CH3:28]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetate2×HCID 24758Sodium hydride2×HCID 21465891HCID 21465891, compound

Product 1

HCID 54345847HCID 54345847, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-chloro-5-(2-chlorophenyl)-2,4-dioxo-1-neopentyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (0.3 g) and chloroacetic acid ethyl ester (0.11 ml) in dimethylformamide (2 ml) was added sodium hydride (60% oil, 40 mg), and the mixture was stirred for 30 minutes at room temperature. To the reaction mixture were further added sodium hydride (40 mg×3) and chloroacetic acid ethyl ester (0.11 ml), which was stirred for 3 hours. To the mixture was then added acetic acid ethyl ester (50 ml), which was washed with water. The solvent was distilled off, and the residue was purified by means of a silica-gel column chromatography (hexane:acetic acid ethyl ester=4:1 v/v as an eluent) to give 0.25 g of colorless crystals, m.p. 152°-153° C.

Workup

  1. stirringwas stirred for 3 hours
  2. washadded acetic acid ethyl ester (50 ml), which was washed with water
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by means of a silica-gel column chromatography (hexane

Sources & evidence

ORD record
ord-a78830388e324c86b22cbbae0f230133
Source dataset
uspto-grants-1997_12
Patent number
US05698691

Reaction notes

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