3,4-Dichloroaniline → HCID 21414091, compound

HRID 442292Notes

Reaction equation

HRID 442292 reaction equation
[CH3:1][S:2]([N:5]([CH3:9])[C:6](Cl)=[O:7])(=[O:4])=[O:3].C(N(CC)CC)C.[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[Cl:25])[NH2:21]>O1CCCC1>[CH3:9][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]([NH:21][C:20]1[CH:22]=[CH:23][C:24]([Cl:25])=[C:18]([Cl:17])[CH:19]=1)=[O:7]

Participants

5

Reactant 3

HCID 72573,4-DichloroanilineHCID 8471TriethylamineHCID 21414088HCID 21414088, compound

Product 1

HCID 21414091HCID 21414091, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 16 g of N-methylsulfonyl-N-methyl-carbamoyl chloride in 100 ml of tetrahydrofuran was slowly added at less than 10° C. to a mixture of 150 ml of tetrahydrofuran, 9.4 g of triethylamine and 15 g of 3,4-dichloroaniline and after stirring for 3 hours, the insolubles were removed by filtration, and the filtrate was concentrated to dryness under reduced pressure to obtain 16 g of N-methyl-N-methylsulfonyl-N'-(3,4-dichlorophenyl)-urea melting at 140° C. Crystallization from ethanol gave an unchanged melting point.

Workup

  1. customthe insolubles were removed by filtration
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d26db59ce849497cb53c08f32564d447
Source dataset
uspto-grants-1977_08
Patent number
US04045209

Reaction notes

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