Chloroacetic anhydride → HCID 22914351, compound

HRID 1378067Notes

Reaction equation

HRID 1378067 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15](=[N:17][OH:18])[NH2:16])=[C:10]3[CH2:9][N:8]([CH3:19])[C:7](=[O:20])[C:6]=2[CH:21]=1.[Cl:22][CH2:23][C:24](OC(=O)CCl)=O>CN(C)C=O>[Cl:22][CH2:23][C:24]1[O:18][N:17]=[C:15]([C:14]2[N:13]=[CH:12][N:11]3[C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:21][C:6]=4[C:7](=[O:20])[N:8]([CH3:19])[CH2:9][C:10]=23)[N:16]=1

Participants

4

Reactant 2

HCID 10946Chloroacetic anhydrideHCID 540046888-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

Product 1

HCID 22914351HCID 22914351, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 5.8 g (0.020 mol) of 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime in 60 ml of dimethylformamide was treated with 3.9 g (0.023 mol) of chloroacetic anhydride. The yellow solution obtained was stirred at 100° for 11/2 hr. and then completely freed from solvents. The oily product crystallized from acetonitrile and was filtered off. The mother liquor was concentrated, the residue was chromatographed over silica gel with dichloromethane/methanol 97:3 as the eluent and the additional portion of product obtained was recrystallized from acetonitrile. There were obtained a total of 4.05 g (59%) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as white crystals; m.p. 245°-247°.

Workup

  1. customThe yellow solution obtained
  2. customThe oily product crystallized from acetonitrile
  3. filtrationwas filtered off
  4. concentrationThe mother liquor was concentrated
  5. customthe residue was chromatographed over silica gel with dichloromethane/methanol 97:3 as the eluent
  6. customthe additional portion of product obtained
  7. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-94386194e6cf4be2b5168283465845e5
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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