1,3-Dichloroacetone → Methyl 3-[4-(hydroxymethyl)-1,3-thiazol-2-yl]benzoate

HRID 1265598Notes

Reaction equation

HRID 1265598 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[S:12])[NH2:11])[CH:5]=1.ClC[C:16](=[O:19])[CH2:17]Cl.[C:20]([O-])(O)=O.[Na+].C[O-].[Na+]>O1CCOCC1.CO>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[S:12][CH:20]=[C:17]([CH2:16][OH:19])[N:11]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 23279244Methyl 3-carbamothioylbenzoate

Product 1

HCID 69688376Methyl 3-[4-(hydroxymethyl)-1,3-thiazol-2-yl]benzoateYield 75.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-thiocarbamoyl-benzoic acid methyl ester (7.8 g), 1,3-dichloro -2-propanone (8.4 g) and NaHCO3 (8.4 g) in 1,4-dioxane (180 mL) was heated to 60° C. for 24 h. The reaction mixture was cooled to 20° C. and added to a stirred solution of NaOMe (5.4 g) in MeOH (200 mL). Stirring was continued for 0.5 h. The mixture was poured into ice-cold 2N HCl (200 mL) and the product was extracted with AcOEt. The organic layer was washed with brine, dried and evaporated in vacuum. The residue was crystallized from CH2Cl2/hexane to give 3-(4-hydroxymethyl-thiazol-2-yl)-benzoic acid methyl ester (7.5 g) as light-brown crystals, mp 115-117° C.

Workup

  1. temperatureThe reaction mixture was cooled to 20° C.
  2. extractionthe product was extracted with AcOEt
  3. washThe organic layer was washed with brine
  4. customdried
  5. customevaporated in vacuum
  6. customThe residue was crystallized from CH2Cl2/hexane

Sources & evidence

ORD record
ord-64c83fac12c6494b91be7e9415a59b05
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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