Sodium Chloride → HCID 59823515, compound

HRID 1426869Notes

Reaction equation

HRID 1426869 reaction equation
[CH2:1]([N:3]([CH3:15])[CH:4]=[N:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([OH:13])=[CH:8][C:7]=1[CH3:14])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:23]1[S:24][C:25]([Cl:30])=[C:26]([CH:28]=[O:29])[N:27]=1.[Na+].[Cl-]>CN(C=O)C.CO.ClCCl>[Cl:30][C:25]1[S:24][C:23]([O:13][C:9]2[C:10]([CH3:12])=[CH:11][C:6]([N:5]=[CH:4][N:3]([CH2:1][CH3:2])[CH3:15])=[C:7]([CH3:14])[CH:8]=2)=[N:27][C:26]=1[CH:28]=[O:29]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 45036952HCID 45036952, compoundHCID 60135688HCID 60135688, compound

Product 1

HCID 59823515HCID 59823515, compoundYield 75.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.57 g (17 mmol) of N-ethyl-N′-(4-hydroxy-2,5-dimethylphenyl)-N-methylimidoformamide in 60 ml of DMF were added 2.51 g (18 mmol) of potassium carbonate and the mixture was stirred at ambient temperature for 30 min. Then 3.00 g (16.5 mmol) of 2,5-dichloro-1,3-thiazole-4-carbaldehyde were added and the mixture was stirred at ambient temperature for 7 days. Then the reaction mixture was poured on water, dichloromethane and some NaCl was added, layers were separated, the water layer was extracted with dichloromethane, the organic phase was dried over sodium sulfate and evaporated. Column chromatographic (gradient: dichloromethane->methanol) yielded 4.40 g (12.5 mmol) 67% of N′-{4-[(5-chloro-4-formyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide log P (pH 2.3)=1.51

Workup

  1. stirringthe mixture was stirred at ambient temperature for 7 days
  2. customlayers were separated
  3. extractionthe water layer was extracted with dichloromethane
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-579a0045a4224084a4d3e204ab7fa2cc
Source dataset
uspto-grants-2015_01
Patent number
US08933107B2

Reaction notes

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