Dimethyl Sulfoxide → HCID 178502518, compound

HRID 1733367Notes

Reaction equation

HRID 1733367 reaction equation
[NH:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[CH:3]1[NH:14][C:15]([NH:17][C:18]([O:20][CH3:21])=[O:19])=[S:16].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CS(C)=O.[OH-].[Na+]>O>[NH:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[CH:3]1[NH:14][C:15](=[N:17][C:18]([O:20][CH3:21])=[O:19])[S:16][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 131711978HCID 131711978, compound

Product 1

HCID 178502518HCID 178502518, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100.0 g (0.33 mole) of imino(2-furylmethyl)-2-(3-carbomethoxythioureido) benzene and 50.0 g. (0.395 mole) of benzyl chloride in 275 ml. of dimethyl sulfoxide is slowly added 15.0 g (0.375 mole) of sodium hydroxide in 260 g. of water. The resulting mixture is stirred for 1/2 hour and the yellow precipitate is separated by filtration and recrystallized from 800 ml of methylene chloride-hexane (1:1) to give 91.1 g (70.1%) of 1-imino-(2-furylmethyl)-2-(3-carbomethoxy-S-benzylisothioureido)benzene m.p. 112°-114° C.

Workup

  1. customthe yellow precipitate is separated by filtration
  2. customrecrystallized from 800 ml of methylene chloride-hexane (1:1)

Sources & evidence

ORD record
ord-2ee070c3a2d84d5d9bd5e6cab58159ea
Source dataset
uspto-grants-1980_12
Patent number
US04241079

Reaction notes

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