p-Toluenesulfonic acid → Methyl 3-(1,3-thiazol-2-yl)benzoate

HRID 1171506Notes

Reaction equation

HRID 1171506 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])(=[S:3])[NH2:2].CO[CH:16](OC)[CH2:17]Cl.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[S:3]1[CH:17]=[CH:16][N:2]=[C:1]1[C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 609862-Chloro-1,1-dimethoxyethaneHCID 23279244Methyl 3-carbamothioylbenzoate

Product 1

HCID 18945333Methyl 3-(1,3-thiazol-2-yl)benzoateYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 0.6 g (0.003 mol) of methyl 3-carbamothioylbenzoate in 6 ml of acetic acid was charged with 1.15 g (0.009 mol) of chloroacetaldehyde dimethyl acetal and a catalytic amount of PTSA. The RM was heated to 100° C. over night. Acetic acid was removed under vacuum and the crude product was purified by 60-120 silica gel column using 5% of ethyl acetate in pet ether as eluent to provide methyl 3-(thiazol-2-yl)benzoate (0.5 g) as a white solid.

Workup

  1. customAcetic acid was removed under vacuum
  2. customthe crude product was purified by 60-120 silica gel column

Sources & evidence

ORD record
ord-8121ecccd0b04cfba17db69224b8c008
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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