Water → 2-(Benzylthio)-N,N-dimethylnicotinamide

HRID 2232160Notes

Reaction equation

CC(C)([O-])C.[K+].[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][N:16]([CH3:26])[C:17]([C:19]1[C:20](Cl)=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:18].O>CN(C)C=O>[CH3:15][N:16]([CH3:26])[C:17]([C:19]1[C:20]([S:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:18]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 25.0 g (223 mmol) of potassium t-butoxide in 100 ml of dimethylformamide was cooled to 0° C. and 22 ml (186 mmol) of benzyl mercaptan added dropwise at 0° C. After addition was complete, the reaction mixture was allowed to warm to 25° C. and stirred at this temperature for 15 minutes. The reaction mixture was then re-cooled to O° C. and 34.0 g (186 mmol) of N,N-dimethyl-2-(chloro)-3-pyridinecarboxamide added in one portion. After an exotherm to 50° C., the mixture was heated at 80° C. for 1.5 hour. The mixture was cooled, poured into 100 ml of water and extracted with ether. The combined organic extracts were washed twice with water, then brine and dried over sodium sulfate. Concentration gave 19.2 g of a viscous yellow oil. IR (Nujol) 1640 (CONMe2) cm-1.

Workup

additionAfter addition
temperatureThe reaction mixture was then re-cooled to O° C
temperatureAfter an exotherm to 50° C., the mixture was heated at 80° C. for 1.5 hour
temperatureThe mixture was cooled
extractionextracted with ether
washThe combined organic extracts were washed twice with water
dry with materialbrine and dried over sodium sulfate
concentrationConcentration

Sources & evidence

ORD record: ord-042d5520300149fe86ad0c0374687dd2
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04786734

Reaction notes

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