Thionyl Chloride → HCID 67251262, compound

HRID 41591Notes

Reaction equation

HRID 41591 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:9]2[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)=[C:5]([CH2:7]O)[N:6]=1.S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl>[Cl:18][CH2:7][C:5]1[N:6]=[C:2]([CH3:1])[S:3][C:4]=1[C:9]1[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67251279(2-Methyl-5-m-tolylthiazol-4-yl)methanol

Product 1

HCID 67251262HCID 67251262, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of (2-methyl-5-m-tolylthiazol-4-yl)methanol (300 mg, 1.37 mmol) in chloroform (10 mL), thionyl chloride (162 mg, 1.37 mmol) was added dropwise at rt and stirred for 30 min and then refluxed for 1 h. The reaction mixture was cooled to rt and absorbed directly on silicagel (10 g). Subsequent flash column chromatography (eluent: 7% ethyl acetate in hexane) yielded the title compound (40 mg, 12%). [LCMS RtF=1.70 min, [M+H]+=238.0; TLC Rf=0.54 (methanol/chloroform 10:90)].

Workup

  1. temperaturerefluxed for 1 h
  2. customabsorbed directly on silicagel (10 g)

Sources & evidence

ORD record
ord-c023b1779c904db28806e60d8136839e
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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