Dimethylcarbamoyl Chloride → N'-(4-{[(3,6-Dichloropyridin-2-yl)methyl]sulfanyl}phenyl)-N,N-dimethylurea

HRID 616840Notes

Reaction equation

HRID 616840 reaction equation
[Cl:1][C:2]1[C:3]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.[CH3:18][N:19]([CH3:23])[C:20](Cl)=[O:21]>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:20](=[O:21])[N:19]([CH3:23])[CH3:18])=[CH:13][CH:12]=2)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 203661654-{[(3,6-Dichloropyridin-2-yl)methyl]sulfanyl}aniline

Product 1

HCID 20366168N'-(4-{[(3,6-Dichloropyridin-2-yl)methyl]sulfanyl}phenyl)-N,N-dimethylurea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-(((3,6-dichloro-2-pyridinyl)methyl)thio)benzenamine (10 grams; 0.035 mole) in 25 ml. of dry pyridine was prepared and dimethyl carbamoyl chloride (3.77 grams; 0.035 mole) added thereto while maintaining the temperature of the reaction mixture at 24°-45° C. The resulting reaction mixture was stirred at ambient temperatures for a period of about 15 hours and then mixed with ice and allowed to stand for a period of about two hours. The aqueous layer was decanted and the residue washed with water and recrystallized twice from ether. As a result of the above operations, the desired N'-(4-(((3,6-dichloro-2-pyridinyl)methyl)thio)phenyl)-N,N-dimethyl urea compound was recovered as a crystalline solid having a melting point of 112°-113.5° C.

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture at 24°-45° C
  2. customThe resulting reaction mixture
  3. additionmixed with ice
  4. waitto stand for a period of about two hours
  5. customThe aqueous layer was decanted
  6. washthe residue washed with water
  7. customrecrystallized twice from ether
  8. customAs a result of the above operations
  9. customthe desired N'-(4-(((3,6-dichloro-2-pyridinyl)methyl)thio)phenyl)-N,N-dimethyl urea compound was recovered as a crystalline solid

Sources & evidence

ORD record
ord-a08a3c5a4a2747f5b7f6b1f794d27b2a
Source dataset
uspto-grants-1978_02
Patent number
US04076719

Reaction notes

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