Water → HCID 21856677, compound

HRID 1665642Notes

Reaction equation

HRID 1665642 reaction equation
C([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])C.[C:10]1([C:16]2[N:17]=[C:18]([NH2:21])[S:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN([CH:28]([CH3:30])C)C(C)C.[OH2:31]>C(Cl)(Cl)Cl>[CH2:28]([O:31][C:7](=[O:8])[CH2:3][C:4]([NH:21][C:18]1[S:19][CH:20]=[C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:17]=1)=[O:5])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 403022-Amino-4-phenylthiazoleHCID 81531DiisopropylethylamineHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 21856677HCID 21856677, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Mono ethyl malonyl chloride (375 mg, 2.49 mmol) was added dropwise to a stirred solution of 4-phenyl-thiazol-2-ylamine (400 mg, 2.26 mmol) and DIEA (733 mg, 5.67 mmol) in CHCl3 (4 mL) at 0° C. and the resulting mixture was stirred for 20 minutes at room temperature. The mixture was diluted with water (5 mL) and extracted with chloroform. The organic layer was washed with saturated sodium bicarbonate solution, brine, dried over Na2SO4, and concentrated to afford 302 mg (46%) of N-(4-phenyl-thiazol-2-yl)-malonamic acid ethyl ester.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated sodium bicarbonate solution, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e8e5eb83f8514da399d69647046d5f9d
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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