Ethyl Acetate → 2-[(n-Butoxycarbonylmethyl)thio]thiazolo[5,4-b]pyridine

HRID 1089753Notes

Reaction equation

HRID 1089753 reaction equation
[SH:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][N:5]=2.C(=O)([O-])[O-].[K+].[K+].[CH2:17]([O:21][C:22](=[O:25])[CH2:23]Cl)[CH2:18][CH2:19][CH3:20].C(OCC)(=O)C>CN(C)C=O>[CH2:17]([O:21][C:22]([CH2:23][S:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][N:5]=2)=[O:25])[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11530Butyl chloroacetateHCID 178527801HCID 178527801, compound

Product 1

HCID 150356882-[(n-Butoxycarbonylmethyl)thio]thiazolo[5,4-b]pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Twenty-four (24) g of 2-mercaptothiazolo[5,4-b]pyridine was dissolved in 300 ml of N,N-dimethylformamide, and 43.3 g of potassium carbonate and 23.65 g of chloroacetic acid n-butyl ester were added to the solution, followed by one-hour stirring at room temperature. Seven hundred (700) ml of ethyl acetate was added to the solution, which was then washed with water three times, dehydrated over magnesium sulfate, dried and distilled to remove the solvent to obtain the title compound (39.9 g, 99%).

Workup

  1. waitfollowed by one-hour
  2. washwas then washed with water three times
  3. customdried
  4. distillationdistilled
  5. customto remove the solvent

Sources & evidence

ORD record
ord-ed83ac47f3434237b034421cb6963d14
Source dataset
uspto-grants-1992_01
Patent number
US05079255

Reaction notes

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