Chloroacetamide → HCID 13280939, compound

HRID 1903633Notes

Reaction equation

HRID 1903633 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[C:7](=[CH:18][NH:19][C:20]=3[CH3:21])[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].Cl[CH2:31][C:32]([NH2:34])=[O:33]>CN(C)C=O.O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[C:7](=[CH:18][N:19]([CH2:31][C:32]([NH2:34])=[O:33])[C:20]=3[CH3:21])[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6580ChloroacetamideHCID 13067111HCID 13067111, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13280939HCID 13280939, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In one portion, 4.0 g (11.7 mmol) of 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo-[3,4-d][2]benzazepine were added to an ice-cooled solution of 1.6 g (14.2 mmol) of potassium t-butoxide in 60 ml of dry dimethylformamide. After stirring at 0° C. for 15 minutes, 1.4 g (15.0 mmol) of 2-chloroacetamide were added, and the resulting solution was stirred for 5 minutes. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate and concentrated at reduced pressure to a red residue. Purification of the residue by column chromatography (silica gel, 100 g; eluent, 50% ether in tetrahydrofuran) gave 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-acetamide as a yellow solid. Recrystallization from ethyl acetate gave colorless needles, mp 142°-145° C.

Workup

  1. stirringthe resulting solution was stirred for 5 minutes
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure to a red residue
  6. customPurification of the residue by column chromatography (silica gel, 100 g; eluent, 50% ether in tetrahydrofuran)

Sources & evidence

ORD record
ord-25294a7a1ab34525827bd379634af9db
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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