4-Toluenesulfonyl chloride → HCID 14369790, compound
Reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH3:12][C:13]1[N:14]=[C:15]([C:24]([NH2:26])=O)[S:16][C:17]=1[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:24]([C:15]1[S:16][C:17]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:13]([CH3:12])[N:14]=1)#[N:26]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
p-Toluenesulfonyl chloride (860 mg) was added to a stirred suspension of 4-methyl-5-(4-pyridinyl)-thiazole-2-carboxamide (450 mg) in dry pyridine (5 ml) under ice-cooling, and the mixture was stirred at 90° C. for 21 hours. The mixture was evaporated to dryness, and the residue was dissolved 2N hydrochloric acid aqueous solution (10-15 ml), washed twice with chloroform, and made alkaline by addition of 2N sodium hydroxide aqueous solution. The resulting precipitates were extracted with chloroform, washed with water, dried over magnesium sulfate, and evaporated to dryness. The residue was washed with petroleum ether, and was recrystallized from iso-propanol (twice) to give 2-cyano-4-methyl-5-(4-pyridinyl)-thiazole (220 mg, yield 53%) as pale yellow needles.
Workup
- temperaturecooling
- customThe mixture was evaporated to dryness
- dissolutionthe residue was dissolved 2N hydrochloric acid aqueous solution (10-15 ml)
- washwashed twice with chloroform
- additionby addition of 2N sodium hydroxide aqueous solution
- customThe resulting precipitates
- extractionwere extracted with chloroform
- washwashed with water
- dry with materialdried over magnesium sulfate
- customevaporated to dryness
- washThe residue was washed with petroleum ether
- customwas recrystallized from iso-propanol (twice)
Sources & evidence
- ORD record
- ord-8bad51cfa40d48488cf96cb4c96f4baa
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04804668
Reaction notes
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