Methylamine → N-methyl-2-chlorothiazole-4-carboxamide

HRID 1470737Notes

Reaction equation

HRID 1470737 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([C:7](Cl)=[O:8])[N:6]=1.[CH2:10]([N:12](CC)CC)C.CN>ClCCl.C1COCC1>[CH3:10][NH:12][C:7]([C:5]1[N:6]=[C:2]([Cl:1])[S:3][CH:4]=1)=[O:8]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 450815362-Chloro-1,3-thiazole-4-carbonyl chloride

Product 1

HCID 53630730N-methyl-2-chlorothiazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 445 mg (2.44 mmol) 2-chloro-thiazole-4-carbonyl chloride in 8.0 mL dichloromethane is added a mixture of 0.38 mL (2.69 mmol) triethylamine and 1.35 mL (2.69 mmol) 2 molars solution of methylamine in THF. The mixture is stirred over night, concentrated and the residue is treated with water and NaHCO3 solution. After extraction with ethylacetate the organic phases are combined, dried (Na2SO4) and concentrated to yield the desired product

Workup

  1. concentrationconcentrated
  2. additionthe residue is treated with water and NaHCO3 solution
  3. extractionAfter extraction with ethylacetate the organic phases
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c3330bf45f2045e28397d1296808a72a
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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