4-Methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-amine → HCID 54562017, compound

HRID 372906Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 5.4 g of 2-(i-propoxycarbonyl) benzenesulfonyl isocyanate (20 mmol) in 5.4 g of 1,2-dichloroethane is added dropwise over the course of 5 min 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 2 h. After removal of the volatiles under waterpump vacuum at 60° C., the residue is stirred with a mixture of ethanol and pentane, when crystallization occurs. The product is filtered off with suction and dried at 50° C. under waterpump vacuum. 6.1 g of the title compound (13 mmol; 66% of theory) are isolated with melting point 182°-185° C.

Workup

waitat 50° C. for 2 h
customAfter removal of the volatiles under waterpump vacuum at 60° C.
stirringthe residue is stirred with a mixture of ethanol and pentane, when crystallization
filtrationThe product is filtered off with suction
customdried at 50° C. under waterpump vacuum

Sources & evidence

ORD record: ord-7a621c89b0134efb8466ee1a14c7ecf9
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05160365

Reaction notes

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