(Diethylamino)sulfur trifluoride → HCID 13125992, compound

HRID 1112099Notes

Reaction equation

HRID 1112099 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH:9](O)[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.C(N(S(F)(F)[F:28])CC)C>C(Cl)Cl>[F:28][CH:9]1[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[C:6]2[CH:21]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[NH:11][C:10]1=[O:12]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 131260123-Hydroxyflubromazepam

Product 1

HCID 13125992HCID 13125992, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 4.2 g (0.012 mole) of 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one in 200 ml methylene chloride was cooled to -70°, and 5 ml (0.04 mole) of diethylaminosulfur trifluoride was added dropwise. The reaction mixture was allowed to warm to -10°, and held at this temperature until most of the solid had dissolved. The reaction mixture was poured into ice-water and stirred vigorously. The organic layer was separated, washed with water, dried (MgSO4) and evaporated to dryness under reduced pressure. The residue was recrystallized from benzene-hexane to give 3.12 g of 3-fluoro-7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one as light yellow crystals: mp 195°-197° (dec.); 19F nmr (DMSO-d6) δ -113.0 ppm (m, 1F) and -162.1 ppm (d, J = 56 Hz, 1F); 1H nmr (DMSO-d6) δ 5.88 ppm (d, J = 56 Hz, 1H), 7.2-7.9 ppm (m, 7H), 11.2 ppm (NH).

Workup

  1. temperaturewas cooled to -70°
  2. temperatureto warm to -10°
  3. dissolutionhad dissolved
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-49a63e7bf70c4b5db5e44a91d92bdfc0
Source dataset
uspto-grants-1978_10
Patent number
US04120856

Reaction notes

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