Ethanol → HCID 15290905, compound

HRID 1735576Notes

Reaction equation

HRID 1735576 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:30]3[CH:31]=[C:32]4[O:37][CH2:36][O:35][C:33]4=[CH:34][C:29]=3[CH2:28][C:27]([CH3:38])=[N:26][N:25]=2)=[CH:20][CH:19]=1.C(O)C>ClCCl>[C:1]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:30]3[CH:31]=[C:32]4[O:37][CH2:36][O:35][C:33]4=[CH:34][C:29]=3[CH2:28][C:27]([CH3:38])=[N:26][N:25]=2)=[CH:20][CH:19]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 35384-(8-Methyl-9H-1,3-dioxolo(4,5-H)(2,3)benzodiazepin-5-yl)benzenamineHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 15290905HCID 15290905, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

1.0 ml (15 mmol) of benzoyl chloride and 2.1 ml (15 mmol) of triethylamine were added to a solution of 4 g (13.6 mmol) of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine in dichloromethane and the reaction mixture was stirred at 25° C. for 24 hours. The solution was extracted with 3×30 ml of water, 3×20 ml of a 4% aqueous sodium hydroxide solution and finally with 2×30 ml of distilled water. The organic layer was dried, evaporated under reduced pressure, then the crystalline residue was treated with 20 ml of hot ethanol to obtain 3.97 g of raw product, m.p. 242°-243° C. This raw product was repeatedly treated with 20 ml of hot ethanol, next day it was filtered at 0°-5° C., washed with 3×3 ml of ethanol and dried at 100° C. to yield 3.85 g (71.3 %) of the pure aimed product, m.p. 246°14 247° C. (decomp.).

Workup

  1. extractionThe solution was extracted with 3×30 ml of water, 3×20 ml of a 4% aqueous sodium hydroxide solution and finally with 2×30 ml of distilled water
  2. customThe organic layer was dried
  3. customevaporated under reduced pressure
  4. additionthe crystalline residue was treated with 20 ml of hot ethanol
  5. customto obtain 3.97 g of raw product, m.p. 242°-243° C
  6. filtrationwas filtered at 0°-5° C.
  7. washwashed with 3×3 ml of ethanol
  8. customdried at 100° C.

Sources & evidence

ORD record
ord-763460e640384bb8bca9837314117479
Source dataset
uspto-grants-1996_07
Patent number
US05536832

Reaction notes

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