Water → HCID 21249983, compound

HRID 1531656Notes

Reaction equation

HRID 1531656 reaction equation
[Br:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=3)=[N:10][N:9]=[C:8]([CH3:21])[CH2:7][C:6]=2[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[CH:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1.O>C1C=CC=CC=1>[Br:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=3)=[N:10][N:9]([C:34]([CH:31]3[CH2:33][CH2:32]3)=[O:35])[C:8]([CH3:21])=[CH:7][C:6]=2[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77637Cyclopropanecarbonyl chlorideHCID 21249973HCID 21249973, compound

Product 1

HCID 21249983HCID 21249983, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.5 g of 7-bromo-1-(4-nitrophenyl)-4-methyl-8-methoxy-5H-2,3-benzodiazepine (Example 3, Step C) is suspended in 15 ml of benzene, mixed with 0.53 g of potassium carbonate and 0.17 ml of cyclopropylcarboxylic acid chloride and then refluxed for 5 hours. Then, the mixture is stirred with water, the organic phase is separated, washed in succession with soda solution and water, dried, filtered and concentrated by evaporation. The residue is purified by absorptive precipitation in ethanol, and 0.38 g of 7-bromo-3-cyclopropylcarbonyl-1-(4-nitrophenyl)-4-methyl-8-methoxy-3H-2,3-benzodiazepine of the title compound with a melting point of 231-223° C. is obtained.

Workup

  1. temperaturerefluxed for 5 hours
  2. customthe organic phase is separated
  3. washwashed in succession with soda solution and water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue is purified by absorptive precipitation in ethanol

Sources & evidence

ORD record
ord-6d546301daec4266a05d92c60bc47078
Source dataset
uspto-grants-2001_03
Patent number
US06200970B1

Reaction notes

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