Acetic Acid → 4-(benzyloxy)-N1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)benzene-1,2-diamine

HRID 1848160ノート

反応式

HRID 1848160 の反応式
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:12]([NH:13][CH2:14][C:15]2[CH:25]=[CH:24][C:18]3[N:19]=[C:20]([S:22][CH3:23])[S:21][C:17]=3[CH:16]=2)=[C:11]([N+:28]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(O)=O.CO>[Zn].C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH2:28])[C:12]([NH:13][CH2:14][C:15]2[CH:25]=[CH:24][C:18]3[N:19]=[C:20]([S:22][CH3:23])[S:21][C:17]=3[CH:16]=2)=[CH:26][CH:27]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 887MethanolHCID 866811284-(benzyloxy)-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-2-nitroaniline

生成物 1

HCID 866811294-(benzyloxy)-N1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)benzene-1,2-diamine収率 95.2%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

To a mixture of 4-(benzyloxy)-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-2-nitroaniline (2.8 g, 6.42 mmol) from the previous step, HOAc (7.5 mL), MeOH (7.5 mL) and DCM (50 mL) at 0° C. was added portionwise zinc dust (4.25 g, 65.4 mmol). The reaction mixture was stirred at 5° C. for 1 h. The mixture was filtered and the filtrate was diluted with DCM and washed sequentially with water and saturated aq NaHCO3. The organic layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 4-(benzyloxy)-N1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)benzene-1,2-diamine (2.49 g, 95%) as a light orange solid which was not purified further. 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=8.4 Hz, 1H), 7.77 (s, 1H), 7.26-7.44 (m, 7H), 6.59 (d, J=8.4 Hz, 1H), 6.46 (s, 1H), 6.38 (m, 1H), 4.97 (s, 2H), 4.34 (s, 2H), 3.54 (br s, 2H), 2.80 (s, 3H). LCMS (ESI) m/z 408 (M+H)+.

後処理

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with DCM
  3. washwashed sequentially with water and saturated aq NaHCO3
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-bc56a2b0d79642a9b233c26d45bd664b
出典データセット
uspto-grants-2015_02
特許番号
US08952058B2

反応ノート

読み込み中…