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

HRID 847362
Notes
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Reaction equation

HRID 847362 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-e017bea866634d8fb94d2a40835be73d
Source dataset
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05141946

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes