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

反応式

HRID 3081 の反応式
[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

参加物

5

反応物 2

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

生成物 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)urea収率 82.1%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-854b8b53d833423eaf0208d0354bd8e9
出典データセット
uspto-grants-1998_03
特許番号
US05733867

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