3-Nitrophenyl isocyanate → N-[1-(1-Adamantylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]-N'-(3-nitrophenyl)urea

HRID 3081

Reaction equation

HRID 3081 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]=[C:11]=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:13]12([CH2:23][N:24]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[N:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:27](=[O:41])[CH:26]([NH2:42])[C:25]3=[O:43])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2>C(#N)C.ClCCl>[C:13]12([CH2:23][N:24]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[N:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:27](=[O:41])[CH:26]([NH:42][C:11]([NH:10][C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)=[O:12])[C:25]3=[O:43])[CH2:22][CH:17]3[CH2:16][CH:15]([CH2:21][CH:19]([CH2:18]3)[CH2:20]1)[CH2:14]2

Participants

5

Reactant 2

HCID 768353-Nitrophenyl isocyanateHCID 109606701-Adamantylmethyl-3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Product 1

HCID 10793342N-[1-(1-Adamantylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]-N'-(3-nitrophenyl)ureaYield 82.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-nitrophenyl isocyanate (0.082 g) in dry acetonitrile (8 ml) was added to a solution of the 1-(1-Adamantylmethyl-3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (0.2 g) in dry acetonitrile (10 ml) under a nitrogen atmosphere. The mixture was stirred at 23° for 2 h, then diluted with dichloromethane (15 ml) and washed with brine (15 ml). The organic solution was dried, concentrated in vacuo and the residue was triturated with diethyl ether to give the title compound as a white solid (0.229 g). M.p. 213°-5°. T.I.c. CH-EA (2:1), Rf0.33.

Workup

  1. washwashed with brine (15 ml)
  2. customThe organic solution was dried
  3. concentrationconcentrated in vacuo
  4. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-854b8b53d833423eaf0208d0354bd8e9
Source dataset
uspto-grants-1998_03
Patent number
US05733867

Linked notes

Loading…