Chloroacetic anhydride → HCID 53864688, compound

HRID 1378091Notes

Reaction equation

HRID 1378091 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][C@H:10]3[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:23][CH2:24][C:25](OC(=O)CCl)=O>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[O:17][C:25]([CH2:24][Cl:23])=[N:19][N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10946Chloroacetic anhydrideHCID 53795200HCID 53795200, compound

Product 1

HCID 53864688HCID 53864688, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.4 g (13.8 mmol) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid hydrazide were stirred at room temperature overnight in 30 ml of N,N-dimethylformamide with 2.65 g (15.5 mmol) of chloroacetic anhydride. After evaporating the solvent the residue was stirred at room temperature for 48 hours with 20 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 and evaporating the solvent there were obtained 3.39 g (60%) of (S)-8-chloro-1-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 185°-189°.

Workup

  1. customAfter evaporating the solvent the residue
  2. additionThe reaction mixture was treated with ice
  3. extractionextracted four times with methylene chloride
  4. dry with materialBy drying the organic phase over magnesium sulfate
  5. customevaporating the solvent there

Sources & evidence

ORD record
ord-ec075c32d9934266a8a86f956f381b37
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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