2-Nitrobenzenesulfenyl chloride → HCID 54127313, compound

HRID 2057350Notes

Reaction equation

HRID 2057350 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]Cl)([O-:15])=[O:14]>CN(C)C=O.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([N:11]([CH3:12])[S:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N+:13]([O-:15])=[O:14])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 243192-Nitrobenzenesulfenyl chlorideHCID 79309N-Methyl-N'-(4-chlorophenyl)urea

Product 1

HCID 54127313HCID 54127313, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

N-4-chlorophenyl-N'-methyl urea (4.1 g) was dissolved in a mixture of dimethylformamide (20 ml) and pyridine (5 ml) and then 2-nitrophenylthiochloride (4.17 g) was added to and dissolved in the solution. After allowing the solution to stand overnight, it was poured into 200 ml of ice-water. The initial product was an oily product which solidified after a while. The solid product was separated by filtration, washed with water and dried. Recrystallization from a mixture of ethyl acetate and n-hexane gave 4.3 g of the object compound. (m.p.: 157°-158° C.)

Workup

  1. dissolutiondissolved in the solution
  2. customThe solid product was separated by filtration
  3. washwashed with water
  4. customdried
  5. customRecrystallization
  6. additionfrom a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-db105315966b48978390eb63ebc55c6b
Source dataset
uspto-grants-1980_07
Patent number
US04210440

Reaction notes

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