2-Chloro-1,1-dimethoxyethane → 2-(N-Methyl-N-phenylamino)thiazole

HRID 2267382

Reaction equation

HRID 2267382 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([NH2:5])=[S:4].CO[CH:14](OC)[CH2:15]Cl>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:3]1[S:4][CH:14]=[CH:15][N:5]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 609862-Chloro-1,1-dimethoxyethaneHCID 7236311-Methyl-1-phenylthiourea

Product 1

HCID 234593752-(N-Methyl-N-phenylamino)thiazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 10 g (60 mmol) of N-methyl-N-phenylthiourea in 100 mL of toluene was treated with 7.2 mL (63 mmol) of chloroacetaldehyde dimethylacetal and heated at reflux for 12 h. The solvent was removed in vacuo and the residue purified by flash chromatography eluting with a linear gradient of 30% EtOAc in hexane to 80% EtOAc in hexane to deliver the title compound. MS (M+H)+ 191.

Workup

  1. temperatureheated
  2. temperatureat reflux for 12 h
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by flash chromatography
  5. washeluting with a linear gradient of 30% EtOAc in hexane to 80% EtOAc in hexane

Sources & evidence

ORD record
ord-c367ec944d73486e8c63d7a0c8109701
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Linked notes

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