Phenyl isocyanate → US10752598, Example 20

HRID 1416112Notes

Reaction equation

HRID 1416112 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[NH:4][C:3]1=[O:20].[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[O:9]=[C:8]1[N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[NH:4][C:3](=[O:20])[CH:2]1[NH:1][C:28]([NH:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:29]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 106832523-Amino-1-phenyl-1,5-dihydrobenzo[b][1,4] diazepine-2,4-dione

Product 1

HCID 10667855US10752598, Example 20Yield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of 3-amino-1-phenyl-1,5-dihydro-benzo [b] [1,4]-diazepine-2,4-dione (0.398 g) in dichloromethane (5 ml) was added phenyl isocyanate (0.177 g) gradually with stirring at ambient temperature. The reaction mixture was stirred two hours at ambient temperature after which time a cream precipitate was separated by filtration to provide the title compound (0.413 g). 1H NMR (300 MHz, DMSO-d6): d 4.97 (d, J=7.5 Hz, 1H), 6.88-6.97 (m, 3H), 7.13-7.47 (m, 12H), 9.16 (s, 1H), 10.78 (br s, 1H); TLC (CH2Cl2 /CH3OH,19:1): Rf =0.21

Workup

  1. stirringThe reaction mixture was stirred two hours at ambient temperature after which time a cream precipitate
  2. customwas separated by filtration

Sources & evidence

ORD record
ord-e7094706bf4d4cb3bf2094393b2e0610
Source dataset
uspto-grants-1999_06
Patent number
US05910495

Reaction notes

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