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

HRID 1357698노트

반응식

HRID 1357698 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b0ac659dcdb3485585065a65ac4afe75
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06593333B1

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