4-Methyl-3-nitroaniline → N-(3-nitro-4-methylphenyl)-3-morpholinobenzamide

HRID 1357698ノート

反応式

HRID 1357698 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](Cl)=[O:11])[CH2:3][CH2:2]1.[CH3:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][CH:15]=[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:8]=2)=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]

参加物

5

反応物 3

HCID 83904-Methyl-3-nitroanilineHCID 8471TriethylamineHCID 220579723-Morpholinobenzoyl chloride

生成物 1

HCID 22057949N-(3-nitro-4-methylphenyl)-3-morpholinobenzamide収率 19.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

3-Morpholinobenzoyl chloride (6.22 g) was added to a solution of 4-methyl-3-nitroaniline (4.20 g) and triethylamine (11.0 ml) in methylene chloride (150 ml) at ambient temperature under argon. The reaction mixture was stirred for 18 hours then diluted to 250 ml with methylene chloride. The mixture was washed with water (3×150 ml) and saturated sodium bicarbonate solution (2×100 ml), dried and evaporated to give a dark brown oil. The oil was triturated with diethyl ether and the solid collected and dried to yield N-(4-methyl-3-nitrophenyl)-3-morpholinobenzamide (1.82g); NMR: (CDCl3) 2.53 (s, 3H), 3.22 (t, 4H), 3.83 (t, 4H), 7.06 (dd, 1H), 7.23 (d, 1H), 7.37 (m, 2H), 7.42 (d, 1H), 7.88 (dd, 1H), 7.97 (s, 1H), 8.21 (d, 1H); m/z 340 (MH+); m.p. 149-150° C.

後処理

  1. washThe mixture was washed with water (3×150 ml) and saturated sodium bicarbonate solution (2×100 ml)
  2. customdried
  3. customevaporated
  4. customto give a dark brown oil
  5. customThe oil was triturated with diethyl ether
  6. customthe solid collected
  7. customdried

出典と根拠

ORDレコード
ord-b0ac659dcdb3485585065a65ac4afe75
出典データセット
uspto-grants-2003_07
特許番号
US06593333B1

反応ノート

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