Chloroacetic anhydride → HCID 54105747, compound

HRID 1378138Notes

Reaction equation

HRID 1378138 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16](=[N:18][OH:19])[NH2:17])=[C:5]2[C@@H:4]2[CH2:20][CH2:21][N:3]12.[Cl:22][CH2:23][C:24](OC(=O)CCl)=O>CN(C)C=O>[Cl:22][CH2:23][C:24]1[O:19][N:18]=[C:16]([C:15]2[N:14]=[CH:13][N:6]3[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:2](=[O:1])[N:3]4[CH2:21][CH2:20][C@H:4]4[C:5]=23)[N:17]=1

Participants

4

Reactant 2

HCID 10946Chloroacetic anhydrideHCID 54277862HCID 54277862, compound

Product 1

HCID 54105747HCID 54105747, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

34.5 g (122 mmol) of (S)-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime were stirred with 23 g (140 mmol) of chloroacetic anhydride in 200 ml of N,N-dimethylformamide at room temperature overnight and at 110° for 2 hours. After evaporating the reaction mixture the residue was dissolved in methylene chloride and the solution was washed with saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel while eluting with methylene chloride/methanol 19/1. There were obtained 24 g (58%) of (S)-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-9-one of m.p. 205°-207°.

Workup

  1. customAfter evaporating the reaction mixture the residue
  2. dissolutionwas dissolved in methylene chloride
  3. washthe solution was washed with saturated sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel
  7. washwhile eluting with methylene chloride/methanol 19/1

Sources & evidence

ORD record
ord-1507dac97b604b3ba33d1ae090c6b7ef
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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