2-Pyrimidinamine, 4-chloro-6-methoxy- → N-[2-(1,2-Dichlorovinyloxy)phenylsulfonyl]-N'-(4-chloro-6-methoxy-pyrimidin-2-yl)urea

HRID 2295471Notes

Reaction equation

HRID 2295471 reaction equation
[Cl:1][C:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([N:15]=[C:16]=[O:17])(=[O:14])=[O:13])=[CH:3][Cl:4].[NH2:18][C:19]1[N:24]=[C:23]([Cl:25])[CH:22]=[C:21]([O:26][CH3:27])[N:20]=1>O1CCOCC1>[Cl:1][C:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]([NH:18][C:19]1[N:24]=[C:23]([Cl:25])[CH:22]=[C:21]([O:26][CH3:27])[N:20]=1)=[O:17])(=[O:13])=[O:14])=[CH:3][Cl:4]

Participants

4

Reactant 2

HCID 798112-Pyrimidinamine, 4-chloro-6-methoxy-HCID 539300762-[(1,2-Dichloroethenyl)oxy]benzene-1-sulfonyl isocyanate

Product 1

HCID 54388028N-[2-(1,2-Dichlorovinyloxy)phenylsulfonyl]-N'-(4-chloro-6-methoxy-pyrimidin-2-yl)urea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7.4 g of 2-(1,2-dichlorovinyloxy)phenylsulfonylisocyanate and 4.0 g of 2-amino-4-chloro-6-methoxypyrimidine are heated to 70°-80° C. in 60 ml of absolute dioxane for 3 hours. After cooling the mixture is treated with activated carbon, filtered and evaporated to 1/5 of the original volume. From the residue crystallise 9.0 g of N-[2-(1,2-Dichlorovinyloxy)phenylsulfonyl]-N'-(4-chloro-6-methoxy-pyrimidin-2-yl)urea, m.p. 196°-198° C.

Workup

  1. temperatureAfter cooling the mixture
  2. additionis treated with activated carbon
  3. filtrationfiltered
  4. customevaporated to 1/5 of the original volume
  5. customFrom the residue crystallise 9.0 g of N-[2-(1,2-Dichlorovinyloxy)phenylsulfonyl]-N'-(4-chloro-6-methoxy-pyrimidin-2-yl)urea, m.p. 196°-198° C.

Sources & evidence

ORD record
ord-b4dc0443c67d4738b179d72cea2b4e54
Source dataset
uspto-grants-1984_01
Patent number
US04425154

Reaction notes

Loading…