3,5-Dichloroaniline → 2-(3,5-Dichlorophenylamino)-4-methylamino-6-chloro-1,3,5-triazine

HRID 520762

Reaction equation

HRID 520762 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7](Cl)[N:6]=[C:5]([Cl:10])[N:4]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[NH2:15].C(Cl)Cl.[K+].[Br-]>>[Cl:11][C:12]1[CH:13]=[C:14]([NH:15][C:7]2[N:8]=[C:3]([NH:2][CH3:1])[N:4]=[C:5]([Cl:10])[N:6]=2)[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

4

Reactant 3

HCID 122813,5-DichloroanilineHCID 3122014,6-dichloro-N-methyl-1,3,5-triazin-2-amineHCID 86707241CH2Cl2 KBr

Product 1

HCID 807686122-(3,5-Dichlorophenylamino)-4-methylamino-6-chloro-1,3,5-triazineYield 10%

Procedure

The title compound was synthesized from 2-methylamino-4,6-dichloro-1,3,5-triazine and 3,5-dichloroaniline using a similar procedure to the one used in 2, except with a longer reaction time (18 h instead of 2 h). Yield: 10%; Tm 242° C.; FTIR (CH2Cl2/KBr) 3275, 3184, 3126, 3081, 2960, 2920, 2849, 1641, 1606, 1573, 1546, 1534, 1507, 1448, 1425, 1388, 1306, 1279, 1253, 1237, 1229, 1205, 1165, 1126, 1115, 1107, 1092, 1035, 984, 954, 937, 869, 854, 837, 809, 793, 753, 725 cm−1; 1H NMR (300 MHz, DMSO-d6, 298 K) δ 10.39, 10.23 (s, s, 1H), 8.24 (s, 1H), 7.86, 7.83 (d, d, 3J=1.8 Hz, 2H), 7.23, 7.20 (t, t, 3J=1.8 Hz, 1H), 2.86, 2.82 (s, d, 3J=4.7 Hz, 3H) ppm; 13C NMR (75 MHz, DMSO-d6): δ 167.7, 165.7, 165.5, 163.6, 162.9, 141.5, 133.83, 133.77, 121.5, 117.8, 117.6, 27.29, 27.23 ppm; HRMS (EI) calcd. for C10H8Cl3N5 (m/e): 302.9845. found: 302.9839.

Workup

  1. customused in 2, except with a longer reaction time (18 h instead of 2 h)
  2. customTm 242° C.

Sources & evidence

ORD record
ord-64b4a77788744cf2b04240c9a6c682fe
Source dataset
uspto-grants-2016_05
Patent number
US09328076B2

Linked notes

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