Heptane → HCID 58399779, compound

HRID 537660Notes

Reaction equation

[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.Cl[C:25]1[N:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:28]=[C:27]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:26]=1.CCCCCCC>C1COCC1.C(O)C.ClCCl>[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:25]2[N:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:28]=[C:27]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:26]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

44.3 g (240 mmol) of N-phenyl-o-phenylenediamine are initially introduced in THF and cooled to 0° C., and 136.4 ml (818 mmol) of N-ethyldiisopropylamine are added dropwise. The mixture is subsequently stirred at room temperature for a further 1 h. A solution of 64.4 g (240 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, dissolved in 1600 ml of THF, is then added dropwise, and the mixture is stirred at 60° C. for 96 h. After cooling, the solution is stirred with 400 ml of heptane, 80 ml of dichloromethane and 100 ml of ethanol. The solid is washed with toluene and washed by stirring with hot heptane, giving 87.7 g (211 mmol) of a crystalline solid. The overall yield is 88%.

Workup

additionis then added dropwise
stirringthe mixture is stirred at 60° C. for 96 h
temperatureAfter cooling
washThe solid is washed with toluene
washwashed
stirringby stirring with hot heptane

Sources & evidence

ORD record: ord-7e95338f771b4a278185053804772dc4
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865321B2

Reaction notes

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