Dimethylformamide → HCID 178454976, compound

HRID 1733368Notes

Reaction equation

HRID 1733368 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].I[CH2:23][CH2:24][CH2:25][CH3:26].CN(C)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][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10962Butyl iodideHCID 14798Sodium HydroxideHCID 131711978HCID 131711978, compound

Product 1

HCID 178454976HCID 178454976, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5.0 g (0.0165 mole) of 1-imino(2-furylmethyl)-2-(3-carbomethoxythioureido)benzene and 3.6 g (0.01975 mole) of iodobutane in 80 ml. of N,N-dimethylformamide is added 0.7 g (0.0175 mole) of sodium hydroxide in 20 ml of water. The resulting mixture is stirred for 1/2 hour and the yellow precipitate that formed is separated by filtration, washed with 50 ml of water and dried to give 3.4 g of crude product, m.p. 86°-7° C. Recrystallization from ether-hexane affords 1-imino(2-furylmethyl)-2-(3-carbomethoxy-S-butylisothioureido)benzene m.p. 84°-85° C.

Workup

  1. customthe yellow precipitate that formed
  2. customis separated by filtration
  3. washwashed with 50 ml of water
  4. customdried
  5. customto give 3.4 g of crude product, m.p. 86°-7° C
  6. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-e0badc51ce4248429aec88cc0f5c603a
Source dataset
uspto-grants-1980_12
Patent number
US04241079

Reaction notes

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