Hydrochloric Acid → N-{4-[2-(3,4-dihydroxyphenyl)-trans-vinyl]benzenesulfonyl}-morpholine

HRID 1866462ノート

反応式

HRID 1866462 の反応式
COC[O:4][C:5]1[CH:6]=[C:7](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([S:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:8]=[CH:9][C:10]=1[O:11]COC.O.Cl.[O-]S([O-])(=O)=O.[Ca+2]>CO.C(Cl)Cl>[OH:4][C:5]1[CH:6]=[C:7](/[CH:15]=[CH:16]/[C:17]2[CH:18]=[CH:19][C:20]([S:23]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)(=[O:25])=[O:24])=[CH:21][CH:22]=2)[CH:8]=[CH:9][C:10]=1[OH:11]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24497Calcium SulfateHCID 68977146N-(4-[2-(3,4-di(methoxymethoxy)phenyl)-trans-vinyl]benzenesulfonyl}morpholine

生成物 1

HCID 57978479N-{4-[2-(3,4-dihydroxyphenyl)-trans-vinyl]benzenesulfonyl}-morpholine収率 91%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

N{4-[2-(3,4-Di(methoxymethoxy)phenyl)-trans-vinyl]benzenesulfonyl} morpholine (0.6 g, 1.3347 mmol) was dissolved in a mixed solvent of MeOH (100 mL) and CH2Cl2 (60 mL). The homogeneous solution was bubbled with argon gas. Water (0.2 g, 11.11 mmol) and concentrated hydrochloric acid (0.9 mL, 10.8 mmol) were added and stirred for 45 hours. The solvents were removed by evaporation and the solid residue was washed with water for several times. The solid was dried under high vacuum in the presence of Drierite providing 0.4388 g of N-{4-[2-(3,4-dihydroxyphenyl)-trans-vinyl]benzenesulfonyl}-morpholine as a yellowish solid (1.214 mmol, yield 91.0%). 1H NMR (Acetone-D6 and DMSO-d6, 300.16 MHz) δ (ppm) 9.05 & 9.03 (2s, 0.64H), 8.81 & 8.79 (2s, 0.65H), 7.81 (d, J=8.5 Hz, 2H), 7.71 (d, J=8.3 Hz, 2H), 7.32 (d, J=16.3 Hz, 1H), 7.13-7.04 (m, 2H), 6.96 (dd, J=8.2 & 1.9 Hz, 1H), 6.80 (d, J=8.3 Hz, 1H), 3.68-3.65 (m, 4H) and 2.94-2.91 (m, 4H). MS (ESI) m/z: 362 (M+1)+, 384 (M+23)+ and 745 (2M+23)+.

後処理

  1. customThe homogeneous solution was bubbled with argon gas
  2. customThe solvents were removed by evaporation
  3. washthe solid residue was washed with water for several times

出典と根拠

ORDレコード
ord-6043e73754db4eaf9bbf73fcc72aa94f
出典データセット
uspto-grants-2009_12
特許番号
US07629375B2

反応ノート

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