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

HRID 1589826Notes

Reaction equation

HRID 1589826 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.[CH2:11]([O:15][C:16](=[O:19])[CH2:17]Cl)[CH2:12][CH2:13][CH3:14].C(OCC)(=O)C>C(=O)([O-])[O-].[K+].[K+]>[CH2:11]([O:15][C:16]([CH2:17][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:19])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11530Butyl chloroacetateHCID 178527801HCID 178527801, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

Twenty-four (24) g of 2-mercaptothiazolo[5,4-b]pyridine was dissolved in 300 ml of N,Ndimethylformamide, 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. additionwere added to the solution
  2. waitfollowed by one-hour
  3. washwas then washed with water three times
  4. customdried
  5. distillationdistilled
  6. customto remove the solvent

Sources & evidence

ORD record
ord-2faec147c499472f96593e2dda2d1f27
Source dataset
uspto-grants-1993_04
Patent number
US05200407

Reaction notes

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