Tetrahydrofuran → HCID 12947065, compound

HRID 839291Notes

Reaction equation

HRID 839291 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([Br:19])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[S:20])[CH2:10][N:9]=1.[OH-].[K+].O1CCCC1.Cl.[CH3:29][N:30]([CH2:32][CH2:33]Cl)[CH3:31]>[Cl-].[Na+]>[CH3:29][N:30]([CH3:31])[CH2:32][CH2:33][S:20][C:11]1[CH2:10][N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:14]2[CH:15]=[C:16]([Br:19])[CH:17]=[CH:18][C:13]=2[N:12]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 12947026HCID 12947026, compound

Product 1

HCID 12947065HCID 12947065, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Procedure

To a solution of 4.4 g of 1,3-dihydro-5-(2-fluorophenyl)-7-bromo-2H-1,4-benzodiazepine-2-thione in a solvent mixture comprising 21.5 ml of a 10% aqueous potassium hydroxide solution and 1.4 ml of tetrahydrofuran is added at room temperature with stirring 2.74 g of N,N-dimethyl-2-chloroethylamine hydrochloride, and the resulting mixture is then stirred at room temperature for 2 hours. The reaction mixture is diluted with an aqueous sodium chloride solution and then extracted with ethyl acetate. The extract is washed with water and dried over magnesium sulfate, and the solvent is removed by distillation under reduced pressure, whereby crude crystalline 2-(2-dimethylaminoethylthio)-5-(2-fluorophenyl)-7-bromo-3H-1,4-benzodiazepine is obtained. Recrystallization from an ether-n-hexane mixture gives 4.05 g of 2-(2-dimethylaminoethylthio)-5-(2-fluorophenyl)-7-bromo-3H-1,4-benzodiazepine, m.p. 105°-107.5° C.

Workup

  1. additionis added at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent is removed by distillation under reduced pressure
  6. customwhereby crude crystalline 2-(2-dimethylaminoethylthio)-5-(2-fluorophenyl)-7-bromo-3H-1,4-benzodiazepine is obtained
  7. customRecrystallization from an ether-n-hexane mixture

Sources & evidence

ORD record
ord-a58f5c3cda544e6bb149a26a460410e6
Source dataset
uspto-grants-1978_06
Patent number
US04094870

Reaction notes

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