Butylamine → 3-(3-Trifluoromethylphenyl)-6-n-butylaminotetrahydro-1,3,5-triazine-2,4-dione

HRID 126760Notes

Reaction equation

[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[F:6][C:7]([F:25])([F:24])[C:8]1[CH:9]=[C:10]([N:14]2[C:19](=[O:20])[NH:18][CH:17](SC)[NH:16][C:15]2=[O:23])[CH:11]=[CH:12][CH:13]=1>C(O)(=O)C>[F:6][C:7]([F:25])([F:24])[C:8]1[CH:9]=[C:10]([N:14]2[C:19](=[O:20])[NH:18][CH:17]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[NH:16][C:15]2=[O:23])[CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 145 °C

Procedure

n-Butylamine (3.92 ml.) was added during 15 minutes to stirred acetic acid (2.4 ml.). After 30 minutes at room temperature, 3-(3-trifluoromethylphenyl)-6-methylthio-tetrahydro-1,3,5-triazine-2,4-dione (6.1 g.) was added to the acetic acid solution. The mixture obtained was then heated at 145° C., for 4 hours. (The liberated methylmercaptan was absorbed into a trap containing an excess of aqueous sodium hydroxide and sodium hypochlorite.) The reaction mixture was cooled to room temperature and then water (75 ml.) was added. The mixture was then stirred for 15 minutes and the white solid which formed was separated by filtration, washed with water (3×150 ml.), and dried (over phosphorus pentoxide) to give 3-(3-trifluoromethylphenyl)-6-n-butylamino-tetrahydro-1,3,5-triazine-2,4-dione (6.0 g., 95%), m.p. 245°-247° C.

Workup

customThe mixture obtained
custom(The liberated methylmercaptan was absorbed into a trap
additioncontaining an excess of aqueous sodium hydroxide and sodium hypochlorite
temperature) The reaction mixture was cooled to room temperature
additionwater (75 ml.) was added
customthe white solid which formed
customwas separated by filtration
washwashed with water (3×150 ml.)
dry with materialdried (over phosphorus pentoxide)

Sources & evidence

ORD record: ord-9490e7a2fd5c4ac0930df0f2154a72ac
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04254122

Reaction notes

Loading…