Water → HCID 15388918, compound

HRID 974986Notes

Reaction equation

HRID 974986 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:12])[CH2:10]Br.Cl.Cl.[NH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[S:23][CH:24]=[C:25]([C:27]3[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=3)[N:26]=2)[CH2:17][CH2:16]1.O>CN(C)C=O>[C:31]([C:30]1[CH:33]=[CH:34][C:27]([C:25]2[N:26]=[C:22]([NH:21][CH:18]3[CH2:19][CH2:20][N:15]([CH2:10][C:9]([O:8][CH3:7])=[O:12])[CH2:16][CH2:17]3)[S:23][CH:24]=2)=[CH:28][CH:29]=1)#[N:32]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 19970304HCID 19970304, compound

Product 1

HCID 15388918HCID 15388918, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

17.75 g of potassium carbonate and 4.3 ml of methylbromoacetate are added to 14.8 g of 4-{2-[(piperid-4-yl) amino]-1,3-thiazol-4-yl}benzonitrile dihydrochloride in 150 ml of N,N-dimethylformamide and the reaction mixture is heated at 50° C. for 2 hours. It is poured over water, extracted with ethyl acetate and the organic phase is washed with water, and then dried over sodium sulphate and concentrated under vacuum. The residue crystallizes from isopropyl ether to give beige crystals which melt at 172° C.; yield 86%.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under vacuum
  5. customThe residue crystallizes from isopropyl ether
  6. customto give beige crystals which
  7. custommelt at 172° C.

Sources & evidence

ORD record
ord-9ef02b971bad422baf2af57c08bd2c86
Source dataset
uspto-grants-1997_03
Patent number
US05607952

Reaction notes

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