4-Methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-amine → i-Propyl 4-chloro-2-[3-(4-methoxy-6-trifluoromethyl-1,3,5-triazin-2-yl)ureidosulfonyl]benzoate

HRID 372907Notes

Reaction equation

HRID 372907 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])=[C:6]([S:8]([N:11]=[C:12]=[O:13])(=[O:10])=[O:9])[CH:7]=1.[NH2:20][C:21]1[N:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23]([C:29]([F:32])([F:31])[F:30])[N:22]=1>ClCCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])=[C:6]([S:8]([NH:11][C:12]([NH:20][C:21]2[N:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23]([C:29]([F:32])([F:31])[F:30])[N:22]=2)=[O:13])(=[O:9])=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 1999484-Methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-amineHCID 13564714(1-Methylethyl)-4-chloro-2-(isocyanatosulfonyl)benzoate

Product 1

HCID 53765058i-Propyl 4-chloro-2-[3-(4-methoxy-6-trifluoromethyl-1,3,5-triazin-2-yl)ureidosulfonyl]benzoateYield 70%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

19.6 g of a solution of 6.1 g of 5-chloro-2-(i-propoxycarbonyl)benzenesulfonyl isocyanate (20 mmol) in 1,2-dichloroethane are added dropwise to a solution of 3.9 g of 2-amino-4-methoxy-6-trifluoromethyl-1, 3,5-triazine (20 mmol) in 150 ml of 1,2-dichloroethane at 25° C. The mixture is stirred at 25° C. for 16 h and then at 50° C. for 3 h. After removal of volatiles under waterpump vacuum at 60° C., the residue is extracted with 200 ml of a mixture of tert-butyl methyl ether and diethyl ether. The solvents are removed under waterpump vacuum at 50° C. and the residue is stirred in a little i-propanol. The solid product is filtered off with suction and dried under waterpump vacuum at 40° C. This results in 7.2 g of the title compound (14 mmol; 70% of theory) of melting point 160°-163° C.

Workup

  1. waitat 50° C. for 3 h
  2. customAfter removal of volatiles under waterpump vacuum at 60° C.
  3. extractionthe residue is extracted with 200 ml of a mixture of tert-butyl methyl ether and diethyl ether
  4. customThe solvents are removed under waterpump vacuum at 50° C.
  5. stirringthe residue is stirred in a little i-propanol
  6. filtrationThe solid product is filtered off with suction
  7. customdried under waterpump vacuum at 40° C

Sources & evidence

ORD record
ord-21266f7bcd1141bdb4f76e4211a17469
Source dataset
uspto-grants-1992_11
Patent number
US05160365

Reaction notes

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