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

HRID 56084

Reaction equation

HRID 56084 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-18f547aa7dbd4e959f7a411db9b1cb6c
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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