Triethylamine → HCID 21249956, compound

HRID 1531658Notes

Reaction equation

HRID 1531658 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][NH:9][CH:8]([CH3:21])[CH2:7][C:6]=2[CH:22]=1.C(N(CC)CC)C.[CH:32]1([C:35](Cl)=[O:36])[CH2:34][CH2:33]1>C(Cl)Cl>[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:35]([CH:32]3[CH2:34][CH2:33]3)=[O:36])[CH:8]([CH3:21])[CH2:7][C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 21249960HCID 21249960, compound

Product 1

HCID 21249956HCID 21249956, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.69 g (1.77 mmol) of 7-bromo-8-methoxy-4-methyl-1-(4-nitrophenyl)-4,5-dihydro-3H-2,3-benzodiazepine (Example 4, Step A) is acylated in methylene chloride (15 ml) in the presence of 0.29 ml (2.1 mmol) of triethylamine with 0.19 ml (2.1 mmol) of cyclopropanoic acid chloride at room temperature for 1.5 hours. After concentration by evaporation and suspension with water, 0.78 g of a crude product, which is purified by suspension in hot ethanol, is obtained. 0.75 g (93%) of 7-bromo-3-cyclopropylcarbonyl-8-methoxy-4-methyl-1-(4-nitrophenyl)-4,5-dihydro-3H-2,3-benzodiazepine with a melting point of 194-196° C. is obtained.

Workup

  1. concentrationAfter concentration
  2. customby evaporation and suspension with water, 0.78 g of a crude product, which
  3. customis purified by suspension in hot ethanol
  4. customis obtained

Sources & evidence

ORD record
ord-7c60cf63ded243b0bfd61274c4f0a350
Source dataset
uspto-grants-2001_03
Patent number
US06200970B1

Reaction notes

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