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

HRID 520765Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH3:17])[N:13]=[C:12](Cl)[N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(Cl)Cl.[K+].[Br-]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH3:17])[N:13]=[C:12]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Reactant 3

HCID 4034-Aminophenol

HCID 807686122-(3,5-Dichlorophenylamino)-4-methylamino-6-chloro-1,3,5-triazine

HCID 86707241CH2Cl2 KBr

Product 1

HCID 867072432-(3,5-Dichlorophenylamino)-4-methylamino-6-(4-hydroxyphenylamino)-1,3,5-triazineYield 74%

Procedure

The title compound was synthesized from 2-(3,5-dichlorophenylamino)-4-methylamino-6-chloro-1,3,5-triazine and 4-aminophenol using a similar procedure to the one used in 8. Yield: 74%; Tg 83° C., Tc 155° C., Tm 187° C.; FTIR (CH2Cl2/KBr) 3401, 3282, 3180, 3112, 2952, 2918, 2850, 1572, 1514, 1503, 1421, 1400, 1366, 1258, 1227, 1168, 1114, 1080, 1011, 993, 937, 833, 807, 737, 703, 668, 632 cm−1; 1H NMR (300 MHz, DMSO-d6, 298 K): δ 9.43 (br s, 0.5H), 9.29 (br s, 0.5H), 9.00 (br s, 0.5H), 8.83 (br s, 0.5H), 7.90 (br d, 2H), 7.43 (br s, 2H), 7.06 (s, 1H), 7.00 (br s, 1H), 6.70 (d, 3J=8.8 Hz, 2H), 2.81 (d, 3J=4.1 Hz, 3H) ppm; 13C NMR (75 MHz, DMSO-d6): δ 165.9, 164.0, 163.6, 152.7, 143.0, 133.6, 131.1, 122.6, 120.0, 117.1, 114.9, 27.2 ppm; HRMS (EI) calcd. for C16H14Cl2N6O (m/e): 376.0606.found: 376.0601.

Workup

customTm 187° C.

Sources & evidence

ORD record: ord-90a68143ff3c46ba80edc57f52bd563e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328076B2

Reaction notes

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