Chloroacetic anhydride → HCID 22914481, compound

HRID 1378096Notes

Reaction equation

HRID 1378096 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH:18][NH2:19])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:22][CH2:23][C:24](OC(=O)CCl)=O>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][C:24]([CH2:23][Cl:22])=[N:19][N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10946Chloroacetic anhydrideHCID 543823867-Chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid hydrazide

Product 1

HCID 22914481HCID 22914481, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.3 g (50 mmol) of 7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-carboxylic acid hydrazide were stirred at room temperature overnight in 160 ml of N,N-dimethylformamide with 9.41 g (55 mmol) of chloroacetic anhydride. After evaporating the solvent the residue was stirred at room temperature over the weekend with 100 ml of a 10% solution of phosphorus pentoxide in methanesulphonic acid. The reaction mixture was treated with ice, made alkaline with conc. sodium hydroxide solution and extracted four times with methylene chloride. By drying the organic phase over magnesium sulfate, evaporation of the solvent and chromatography of the residue on silica gel while eluting with ethyl acetate there were obtained 9.7 g (53%) of 7-chloro-3-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 201°-203°.

Workup

  1. customAfter evaporating the solvent the residue
  2. additionThe reaction mixture was treated with ice
  3. extractionextracted four times with methylene chloride
  4. customBy drying the organic phase
  5. customover magnesium sulfate, evaporation of the solvent and chromatography of the residue on silica gel
  6. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-f41fdb2ffbaf4857aa3dd9e5c86d577f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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