Water → HCID 178482318, compound

HRID 1388970Notes

Reaction equation

HRID 1388970 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 recrystallised 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-baa46bf1df7345e0b726c96a626be6be
Source dataset
uspto-grants-1981_01
Patent number
USRE030473

Reaction notes

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