4-(8-Methyl-9H-1,3-dioxolo(4,5-H)(2,3)benzodiazepin-5-yl)benzenamine → HCID 19040677, compound

HRID 1683707Notes

Reaction equation

HRID 1683707 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:18]3[CH:19]=[C:20]4[O:25][CH2:24][O:23][C:21]4=[CH:22][C:17]=3[CH2:16][C:15]([CH3:26])=[N:14][N:13]=2)=[CH:8][CH:7]=1>CN(C)C=O.O>[CH3:1][NH:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:18]3[CH:19]=[C:20]4[O:25][CH2:24][O:23][C:21]4=[CH:22][C:17]=3[CH2:16][C:15]([CH3:26])=[N:14][N:13]=2)=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 2

HCID 35384-(8-Methyl-9H-1,3-dioxolo(4,5-H)(2,3)benzodiazepin-5-yl)benzenamineHCID 12228Methyl Isocyanate

Product 1

HCID 19040677HCID 19040677, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

0.8 ml (13.4 mmol) of methyl isocyanate was added to a solution containing 1.0 g (3.41 mmol) of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine in 8 ml of dimethylformamide (DMF), then the reaction mixture was stirred at 25° C. for 24 hours. After diluting with 80 ml of water, filtering at 5° C. and drying at 60 to 100° C., 1.06 g of raw product, m.p.: 204°-207° C. (sintering from 160° C.) were obtained which, when recrystallized from 5 ml of ethanol, gave 0.85 g (71.4%) of-the aimed product, m.p.: 223°-224° C. (decomp.).

Workup

  1. filtrationfiltering at 5° C.
  2. customdrying at 60 to 100° C.
  3. custom1.06 g of raw product, m.p.: 204°-207° C. (sintering from 160° C.) were obtained which, when
  4. customrecrystallized from 5 ml of ethanol

Sources & evidence

ORD record
ord-320e63e6cf01411095f07ff760838045
Source dataset
uspto-grants-1997_06
Patent number
US05639751

Reaction notes

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