p-Toluenesulfonic acid → 4-(1,3-Thiazol-2-yl)phenol

HRID 56084

반응식

HRID 56084 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[S:8])[NH2:7])=[CH:4][CH:3]=1.Br[CH2:12][CH:13](OC)OC.CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:8][CH:12]=[CH:13][N:7]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 816722-Bromo-1,1-dimethoxyethaneHCID 27593444-Hydroxythiobenzamide

생성물 1

HCID 2238404-(1,3-Thiazol-2-yl)phenol

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a mixture of 4-hydroxybenzothioamide (30.64 g, 0.20 mol) and 2-bromo-1,1-dimethoxyethane (31.00 g, 0.20 mol) in EtOH (600 mL) was added 4-methylbenzenesulfonic acid (34.44 g, 0.20 mol) with stirring at rt. The reaction mixture was heated at 90° C. for 24 h, then cooled to rt and concentrated in vacuo. The mixture was diluted with H2O (200 mL), adjusted to pH 10 with saturated NaHCO3 aqueous solution and extracted with DCM (200 mL×3). The combined organic phases were concentrated in vacuo to give the title compound as s yellow solid (21.3 g, 60%).

후처리

  1. temperatureThe reaction mixture was heated at 90° C. for 24 h
  2. temperaturecooled to rt
  3. concentrationconcentrated in vacuo
  4. additionThe mixture was diluted with H2O (200 mL)
  5. extractionextracted with DCM (200 mL×3)
  6. concentrationThe combined organic phases were concentrated in vacuo

출처 및 근거

ORD 기록
ord-18f547aa7dbd4e959f7a411db9b1cb6c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

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