Flutemazepam → HCID 13125990, compound

HRID 1389812Notes

Reaction equation

HRID 1389812 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[N:4]([CH3:21])[C:3]1=[O:22].C(N(S(F)(F)[F:29])CC)C>C(Cl)Cl>[F:29][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[N:4]([CH3:21])[C:3]1=[O:22]

Participants

4

Reactant 2

HCID 40344FlutemazepamHCID 123472(Diethylamino)sulfur trifluoride

Product 1

HCID 13125990HCID 13125990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.4 g of 3-hydroxy-1,3-dihydro-1-methyl-7-chloro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one in 10 ml of methylene chloride was added dropwise to a stirred solution of 1.5 ml of diethylaminosulfur trifluoride in 50 ml methylene chloride cooled to -70°. The reaction mixture was allowed to warm slowly to 5° and then poured into 100 ml of ice water. The lower organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. The residue was recrystallized from heptane to give 1.17 g of 3-fluoro-1,3-dihydro-1-methyl-7-chloro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one as cream-colored crystals: mp 91°-95°; 1H nmr (CCl3D) δ 3.51 ppm (s, 3H), 5.66 ppm (d, J=57 Hz, 1H) and 7.5 ppm (m, 7H).

Workup

  1. temperaturecooled to -70°
  2. temperatureto warm slowly to 5°
  3. customThe lower organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-d1ca8305812b48fd8711a5f649d3bfb4
Source dataset
uspto-grants-1981_01
Patent number
US04246270

Reaction notes

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