Sodium hydride → HCID 21529152, compound

HRID 1658319Notes

Reaction equation

HRID 1658319 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][SH:8])=[CH:5][CH:4]=1.[H-].[Na+].Br[C:14]1[C:15]([C:20]([NH2:22])=[O:21])=[N:16][CH:17]=[CH:18][CH:19]=1>CS(C)=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][S:8][C:14]2[C:15]([C:20]([NH2:22])=[O:21])=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 215291573-Bromopicolinamide

Product 1

HCID 21529152HCID 21529152, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

By the procedure of Efxample 1, a solution of p-methoxybenzyl mercaptan in dimethylsulfoxide is added slowly to a stirred suspension of sodium hydride in dry dimethylsulfoxide under nitrogen. After stirring for one hour at room temperature, 3-bromopicolinamide is added and the mixture is kept about 75°C. for three hours, then worked up by cooling, diluting with ice water, filtering off the resulting solid, washing it with water, drying and recrystallizing from aqueous dimethylformamide to give 3-(p-methoxybenzylthio)picolinamide, m.p. 252°C. (dec.).

Workup

  1. waitthe mixture is kept about 75°C. for three hours
  2. temperatureby cooling
  3. filtrationfiltering off the resulting solid
  4. washwashing it with water
  5. customdrying
  6. customrecrystallizing from aqueous dimethylformamide

Sources & evidence

ORD record
ord-463d158b571744ac8104e8bac07acb4f
Source dataset
uspto-grants-1976_06
Patent number
US03963733

Reaction notes

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