Methyl iodide → Methyl 4-benzylthionicotinate

HRID 35542Notes

Reaction equation

HRID 35542 reaction equation
[CH2:1]([C:8]1[C:13]([C:14]([OH:16])=[S:15])=[CH:12][N:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17]I>C(#N)C.O>[CH2:1]([C:8]1[C:13]([C:14]([O:16][CH3:17])=[S:15])=[CH:12][N:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178526145HCID 178526145, compound

Product 1

HCID 54293912Methyl 4-benzylthionicotinate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 2.45 g (0.01 mole) of 4-benzylthionicotinic acid in 35 mL of dry acetonitrile was treated with 1.52 g (0.01 mole) of 1,8-diazabicyclo[5,4,0]under-7-ene (DBU). 1.7 g (0.01 mole) of methyl iodide was added and stirring was continued for 7 hours. The reaction was carefully diluted with water to crystallize 430 mg of methyl 4-benzylthionicotinate which melted at 98°-99° C.

Workup

  1. customto crystallize 430 mg of methyl 4-benzylthionicotinate which melted at 98°-99° C.

Sources & evidence

ORD record
ord-2ee8bb67201f45ee833dcb4a235fffc8
Source dataset
uspto-grants-1988_08
Patent number
US04767766

Reaction notes

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