Water → HCID 178482318, compound

HRID 1834143Notes

Reaction equation

HRID 1834143 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:6]=2[CH:20]=1.[CH3:21][NH2:22].O>O1CCCC1.C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:22][CH3:21])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:6]=2[CH:20]=1

Participants

7

Reactant 3

HCID 962WaterHCID 4540NorfludiazepamHCID 6329Methylamine

Product 1

HCID 178482318HCID 178482318, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

i. A solution of 200 g of 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one in 2 liters of tetrahydrofuran and 250 ml of benzene was saturated with methylamine with cooling in an ice-bath. A solution of 190 g of titanium tetrachloride in 250 ml of benzene was added through a dropping funnel within 15 minutes. After completion of the addition, the mixture was stirred and refluxed for 3 hours. 600 ml of water were added slowly to the cooled mixture. The inorganic material was separated by filtration and was washed well with tetrahydrofuran. The water layer was separated and the organic phase dried over sodium sulphate and evaporated. The crystalline residue was collected to give 7-chloro-5-(2-fluorophenyl)-2-methylamino-3H-1,4-benzodiazepine of melting point 204°-206° C. An analytical sample was recrystallized from methylene chloride/ethanol and had a melting point of 204°-206° C.

Workup

  1. temperaturewith cooling in an ice-bath
  2. additionAfter completion of the addition
  3. temperaturerefluxed for 3 hours
  4. customThe inorganic material was separated by filtration
  5. washwas washed well with tetrahydrofuran
  6. customThe water layer was separated
  7. dry with materialthe organic phase dried over sodium sulphate
  8. customevaporated
  9. customThe crystalline residue was collected

Sources & evidence

ORD record
ord-52b53c9539574b5f8d611177cbf8c79e
Source dataset
uspto-grants-1978_01
Patent number
US04069229

Reaction notes

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