Water → N-(4-Chloro-benzyloxy)-2-(4-cyano-benzylamino)-benzamide

HRID 1663164Notes

Reaction equation

HRID 1663164 reaction equation
O=C1[N:7]([CH2:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[C:4](=[O:21])O1.Cl.[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28][O:29][NH2:30])=[CH:26][CH:25]=1.C(N(C(C)C)C(C)C)C.O>CN(C=O)C>[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28][O:29][NH:30][C:4](=[O:21])[C:5]2[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=2[NH:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 217573Hydroxylamine, O-((4-chlorophenyl)methyl)-, hydrochloride (1:1)HCID 589898174-(2,4-Dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-benzonitrile

Product 1

HCID 58989877N-(4-Chloro-benzyloxy)-2-(4-cyano-benzylamino)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred mixture of 4-(2,4-dioxo-4H-benzo[d][1,3]oxazin-1-ylmethyl)-benzonitrile (Preparation 7D, 319 mg) and O-(4-chloro-benzyl)-hydroxylamine hydrochloride (preparation 9, 267 mg) in DMF (10 ml) was added N-ethyldiisopropylamine (0.4 ml). The reaction mixture was heated to 100° C. and stirred for 17 hours. The mixture was cooled to room temperature and water was added. The pale brown precipitated material was isolated by filtration and re-crystallised from ethanol and gave the title compound as a white solid material. 13C-NMR (DMSO-d6) δ 148.2, 145.9, 135.1, 132.8, 132.5, 132.3, 130.6, 128.2, 128.0, 127.7, 118.8, 114.8, 113.2, 111.4, 109.5, 75.9, 45.4.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe pale brown precipitated material was isolated by filtration
  3. customre-crystallised from ethanol

Sources & evidence

ORD record
ord-d224d29eec114b578e4bb08fbcd6d169
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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