4-Aminophenol → 2-(3,5-Dimethoxyphenylamino)-4-methylamino-6-(4-hydroxyphenylamino)-1,3,5-triazine

HRID 520766Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[N:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14](Cl)[N:13]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(Cl)Cl.[K+].[Br-]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[N:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[N:13]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

Reactant 3

HCID 4034-Aminophenol

HCID 807602312-(3,5-Dimethoxyphenylamino)-4-methylamino-6-chloro-1,3,5-triazine

HCID 86707241CH2Cl2 KBr

Product 1

HCID 867072442-(3,5-Dimethoxyphenylamino)-4-methylamino-6-(4-hydroxyphenylamino)-1,3,5-triazineYield 80%

Procedure

The title compound was synthesized from 2-(3,5-dimethoxyphenylamino)-4-methylamino-6-chloro-1,3,5-triazine and 4-aminophenol using a similar procedure to the one used in 7. Yield: 80%; Tg 81° C.; FTIR (CH2Cl2/KBr) 3401, 3288, 3133, 3003, 2958, 2915, 2840, 1587, 1507, 1481, 1450, 1427, 1400, 1360, 1294, 1264, 1234, 1205, 1177, 1153, 1106, 1082, 1065, 1014, 980, 927, 834, 808, 737, 703, 682, 661 cm−1; 1H NMR (300 MHz, DMSO-d6, 298 K): δ 9.02 (s, 1H), 8.95 (br s, 0.5H), 8.82 (br s, 1H), 8.64 (br s, 0.5H), 7.49 (br s, 2H), 7.09 (br d, 2H), 6.86 (br s, 1H), 6.66 (d, 3J=8.8 Hz, 2H), 6.08 (s, 1H), 3.69 (s, 6H), 2.81 (br s, 3H) ppm; 13C NMR (75 MHz, DMSO-d6): δ 166.0, 164.1, 163.8, 160.2, 152.4, 142.1, 131.6, 122.3, 114.7, 98.0, 93.7, 54.9, 27.3 ppm; HRMS (EI) calcd. for C18H20N6O3 (m/e): 368.1597. found: 368.1609.

Sources & evidence

ORD record: ord-cea9af84e62247e192238757d91573d0
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328076B2

Reaction notes

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