Dichloromethane → N-Methoxy-N,2,4-trimethylthiazole-5-carboxamide

HRID 627511Notes

Reaction equation

HRID 627511 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.C(Cl)Cl.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:27][NH:28][O:29][CH3:30]>O.[OH-].[Na+].CN(C=O)C>[CH3:30][O:29][N:28]([CH3:27])[C:8]([C:4]1[S:3][C:2]([CH3:1])=[N:6][C:5]=1[CH3:7])=[O:10]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 736488Dimethyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 10559951N-Methoxy-N,2,4-trimethylthiazole-5-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a flask containing 2,4-dimethylthiazole-5-carboxylic acid (2.50 g, 15.9 mmol) was added DCM (75 mL) and DMF (3 mL) to afford a homogeneous solution. Then, carbonyldiimidazole (2.84 g, 17.5 mmol) was added and the mixture was stirred at room temperature for 2 hours. N,O-dimethylhydroxylamine hydrochloride (1.90 g, 19.9 mmol) was then added and the reaction mixture was stirred at room temperature for 18 hours, then diluted with water and 1 N NaOH and extracted with DCM (4×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica gel (10-40% EtOAc-DCM) provided the title compound as a colorless oil.

Workup

  1. customto afford a homogeneous solution
  2. stirringthe reaction mixture was stirred at room temperature for 18 hours
  3. extractionextracted with DCM (4×50 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e842f10c2172406d87f6df573b96c86e
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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