4-Chloro-6-methoxy-1,3,5-triazin-2-amine → N-(2-difluoromethoxyphenylsulfonyl)-N'-(4-chloro-6-methoxy-1,3,5-triazin-2-yl)-urea

HRID 2309158Notes

Reaction equation

HRID 2309158 reaction equation
[F:1][CH:2]([F:16])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]=[C:14]=[O:15])(=[O:12])=[O:11].[NH2:17][C:18]1[N:23]=[C:22]([Cl:24])[N:21]=[C:20]([O:25][CH3:26])[N:19]=1>O1CCOCC1>[F:16][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]([NH:17][C:18]1[N:23]=[C:22]([Cl:24])[N:21]=[C:20]([O:25][CH3:26])[N:19]=1)=[O:15])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 236894-Chloro-6-methoxy-1,3,5-triazin-2-amineHCID 110969602-Difluoromethoxybenzenesulfonylisocyanate

Product 1

HCID 13729470N-(2-difluoromethoxyphenylsulfonyl)-N'-(4-chloro-6-methoxy-1,3,5-triazin-2-yl)-ureaYield 87.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

124.6 g of 2-difluoromethoxyphenyl-sulfonyl isocyanate in 100 ml of dioxane are added dropwise to a suspension of 80.3 g of 2-amino-4-chloro-6-methoxy-1,3,5-triazine in 400 ml of absolute dioxane in the course of 10 minutes. The reaction mixture is warmed to 90°-100° for 3 hours, and the solution is then cooled and concentrated to give 180 g of N-(2-difluoromethoxyphenyl-sulfonyl)-N'-(4-chloro-6-methoxy-1,3,5-triazin-2-yl)-urea of melting point 167°-168°.

Workup

  1. temperatureThe reaction mixture is warmed to 90°-100° for 3 hours
  2. temperaturethe solution is then cooled
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ab4051b140e7444a9644d8a2f80bdc7b
Source dataset
uspto-grants-1987_09
Patent number
US04693741

Reaction notes

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