Chloroacetic anhydride → HCID 22914464, compound

HRID 1378093Notes

Reaction equation

HRID 1378093 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]([NH:19][NH2:20])=[O:18])=[C:4]2[CH2:3]1.[Cl:21][CH2:22][C:23](OC(=O)CCl)=O>CN(C)C=O>[Cl:21][CH2:22][C:23]1[O:18][C:17]([C:16]2[N:15]=[CH:14][N:5]3[C:6]4[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=4[C:8](=[O:9])[N:2]([CH3:1])[CH2:3][C:4]=23)=[N:19][N:20]=1

Participants

4

Reactant 2

HCID 10946Chloroacetic anhydrideHCID 67713563HCID 67713563, compound

Product 1

HCID 22914464HCID 22914464, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.4 g (34.7 mmol) of 5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid hydrazide were stirred at room temperature for 3 hours in 75 ml of N,N-dimethyl- formamide with 27.1 g (41.5 mmol) of chloroacetic anhydride. After evaporating the solvent the residue was stirred at room temperature overnight with 75 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 6.9 g (61%) of 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. 221°-222°.

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-fa111943f86547f4904076e59292fd5d
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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