N-Desalkyl-3-hydroxyflurazepam → HCID 13125988, compound
Reaction equation
O[CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:6]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:5]=2[NH:4][C:3]1=[O:21].C(N(S(F)(F)[F:28])CC)C>C(Cl)Cl>[F:28][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:6]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:5]=2[NH:4][C:3]1=[O:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A well stirred suspension of 3.0 g (0.01 mole) of 3-hydroxy-1,3-dihydro-7-chloro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one in 150 ml of methylene chloride was cooled to -70°, and 7.5 ml (0.06 mol) of diethylaminosulfur trifluoride was added dropwise over a period of 10 min. The reaction mixture was then allowed to warm slowly over a period of 26 min. to -10° and then poured into 200 ml of ice water. The organic layer was separated, dried over MgSO4, and evaporated to dryness under reduced pressure to give 2.95 g (98%) of crude product. Recrystallization from benzene-heptane gave 2.00 g (67%) of 3-fluoro-1,3-dihydro-7-chloro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one as off-white crystals: mp 206°-207° (dec); 1H nmr (DMSO-d6) δ 5.95 ppm (d, J=56 Hz, 1H), 7.47 ppm (n, 7H), 11.25 ppm (s, 1H); 19F nmr (DMSO-d6) δ -162.0 ppm (d, J=56 Hz, 1F) and δ -113.0 ppm (m, 1F).
Workup
- temperaturewas cooled to -70°
- temperatureto warm slowly over a period of 26 min. to -10°
- customThe organic layer was separated
- dry with materialdried over MgSO4
- customevaporated to dryness under reduced pressure
- customto give 2.95 g (98%) of crude product
- customRecrystallization from benzene-heptane
Sources & evidence
- ORD record
- ord-0d3724bbdf67468497259091505ed600
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04246270
Reaction notes
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