2-Thiazolemethanol, 4-(2-chlorophenyl)-, 2-methanesulfonate → 4-(2-Chlorophenyl)-1,3-thiazole-2-carbaldehyde

HRID 1944500Notes

Reaction equation

HRID 1944500 reaction equation
CS([O:5][CH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[N:11]=1)(=O)=O>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[N:11]=[C:7]([CH:6]=[O:5])[S:8][CH:9]=1

Participants

4

Reactant 1

HCID 591874322-Thiazolemethanol, 4-(2-chlorophenyl)-, 2-methanesulfonate

Product 1

HCID 34461034-(2-Chlorophenyl)-1,3-thiazole-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(4-(2-Chlorophenyl)thiazol-2-yl)methyl methane-sulfonate 4 from Step C above (0.10 g, 0.51 mmol) is dissolved in dichloromethane (4.0 mL), followed by addition of manganese dioxide (0.18 g, 2 mmol). The suspension is vigorously stirred at room temperature overnight. Filtration and concentration yielded 4-(2-chlorophenyl)thiazole-2-carbaldehyde 5 as a light-brown oil: MS calcd. for C10H7ClNOS (M+H+) 224.0. found 224.0.

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-8d96d17932a449e39ada97ac7021d1fa
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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