3,4,5-Trimethoxyaniline → 2-(3,4,5-Trimethoxyphenylamino)-4-methylamino-6-chloro-1,3,5-triazine

HRID 520764

Reaktionsgleichung

Reaktionsgleichung von HRID 520764
[CH3:1][NH:2][C:3]1[N:8]=[C:7](Cl)[N:6]=[C:5]([Cl:10])[N:4]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[NH2:16].C(Cl)Cl.[K+].[Br-]>>[CH3:23][O:22][C:18]1[CH:17]=[C:15]([NH:16][C:7]2[N:8]=[C:3]([NH:2][CH3:1])[N:4]=[C:5]([Cl:10])[N:6]=2)[CH:14]=[C:13]([O:12][CH3:11])[C:19]=1[O:20][CH3:21]

Komponenten

4

Edukt 3

HCID 322853,4,5-TrimethoxyanilineHCID 3122014,6-dichloro-N-methyl-1,3,5-triazin-2-amineHCID 86707241CH2Cl2 KBr

Produkt 1

HCID 867072422-(3,4,5-Trimethoxyphenylamino)-4-methylamino-6-chloro-1,3,5-triazineAusbeute 65 %

Versuchsvorschrift

The title compound was synthesized from 2-methylamino-4,6-dichloro-1,3,5-triazine and 3,4,5-trimethoxyaniline using a similar procedure to the one used in 2. Yield: 65%; Tm 237° C.; FTIR (CH2Cl2/KBr) 3270, 3134, 3051, 2964, 2940, 2842, 2831, 1658, 1631, 1612, 1588, 1567, 1535, 1502, 1453, 1422, 1390, 1351, 1297, 1264, 1230, 1201, 1189, 1172, 1128, 1082, 1057, 1034, 997, 978, 924, 882, 830, 809, 735, 704, 679 cm−1; 1H NMR (300 MHz, DMSO-d6, 298 K) δ 9.97, 9.77 (s, s, 1H), 8.09, 7.91 (s, s, 1H), 7.21, 7.09 (s, s, 2H), 3.74 (s, 6H), 3.61 (s, 3H), 2.86, 2.80 (d, d, 3J=4.6 Hz, 3H) ppm; 13C NMR (75 MHz, DMSO-d6): δ 167.4, 165.8, 165.6, 163.3, 162.9, 152.5, 135.0, 134.8, 133.2, 133.0, 98.2, 97.6, 60.0, 55.8, 55.5, 27.4, 27.2 ppm; HRMS (EI) calcd. for C13H16ClN5O3 (m/e): 325.0942. found: 325.0934.

Aufarbeitung

  1. customTm 237° C.

Quellen und Nachweise

ORD-Eintrag
ord-bea3855a875f4c48b6bef688e2543379
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328076B2

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