Trifluoroacetic anhydride → HCID 20295645, compound

HRID 1389817Notes

Reaction equation

HRID 1389817 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N+:8]([O-])=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1.[F:22][C:23]([F:34])([F:33])[C:24]([O:26]C(=O)C(F)(F)F)=[O:25]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH:9]([O:26][C:24](=[O:25])[C:23]([F:34])([F:33])[F:22])[N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1

Participants

3

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 178516819HCID 178516819, compound

Product 1

HCID 20295645HCID 20295645, compoundYield 80%

Procedure

A 9.5-g (0.027 mole) portion of 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one 4-oxide was added portion-wise to 50 ml of trifluoroacetic anhydride, and the reaction mixture was stirred for 90 minutes. The suspended solid that formed was collected on a filter, washed thoroughly with pentane and dried in a vacuum over KOH. There was obtained 9.72 g (80%) of 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-3-trifluoroacetoxy-2H-1,4-benzodiazepin-2-one as an off-white crystalline powder: mp 175°-177° (dec.); 19F nmr (DMSO-d6) δ -74.6 ppm (s, 3F) and -112.7 ppm (m, 1F); 1H nmr (DMSO-d6) δ 6.34 ppm (s, 1H), 7.1-8.1 ppm (m, 7H), 11.5 ppm (NH).

Workup

  1. customThe suspended solid that formed
  2. customwas collected on a filter
  3. washwashed thoroughly with pentane
  4. dry with materialdried in a vacuum over KOH

Sources & evidence

ORD record
ord-deb05ca0e0e2480eac6b6b92ae539fd5
Source dataset
uspto-grants-1981_01
Patent number
US04246270

Reaction notes

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