Dimethylformamide → N-(1-butanesulfonyl)-4-acetylamino-3-nitrobenzamide

HRID 1699640

反応式

HRID 1699640 の反応式
CN(C)C=O.[C:6]([NH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20])(=[O:8])[CH3:7].[CH2:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH2:23][CH2:24][CH3:25].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O.C(Cl)(Cl)Cl>[CH2:22]([S:26]([NH:29][C:14](=[O:16])[C:13]1[CH:17]=[CH:18][C:10]([NH:9][C:6](=[O:8])[CH3:7])=[C:11]([N+:19]([O-:21])=[O:20])[CH:12]=1)(=[O:28])=[O:27])[CH2:23][CH2:24][CH3:25]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 184601-ButanesulfonamideHCID 737584-Acetamido-3-nitrobenzoic acidHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

生成物 1

HCID 18680978N-(1-butanesulfonyl)-4-acetylamino-3-nitrobenzamide収率 70.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

N,N′-carbonyldiimidazole (9.40 g) is added to an N,N-dimethylformamide (300 ml) solution of 4-acetylamino-3-nitro-benzoic acid (10.0 g), and the solution is stirred for 1 hour at room temperature. Then, 1-butanesulfonamide (7.92 g) and diazabicycloundecene (8.83 g) are added into the solution, and the solution is stirred for 72 hours at 100° C. After chloroform and water are added into the solution and the solution is separated into layers, the residue, which is obtained by concentrating the organic layer, is purified using silica gel column chromatography (eluate: ethyl acetate/methanol=4/1), and thus, N-(1-butanesulfonyl)-4-acetylamino-3-nitrobenzamide (10.75 g) is obtained. 1H-NMR (DMSO-d6, δ): 0.87 (3H, t, J=7.4 Hz), 1.37-1.44 (2H, m), 1.64-1.71 (2H, m), 2.12 (3H, s), 3.52 (2H, t, J=7.7 Hz), 7.83 (1H, d, J=8.6 Hz), 8.21 (1H, dd, J=8.6 and 2.1 Hz), 8.54 (1H, d, J=2.2 Hz), 10.56 (1H, s), 12.32 (1H, s).

後処理

  1. stirringthe solution is stirred for 72 hours at 100° C
  2. customthe solution is separated into layers
  3. customthe residue, which is obtained
  4. concentrationby concentrating the organic layer
  5. customis purified

出典と根拠

ORDレコード
ord-c6b5408aa689489d99c4c281a89c5861
出典データセット
uspto-grants-2002_02
特許番号
US06348032B1

関連ノート

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