N,N-dimethyl-m-phenylenediamine → N-(3-(dimethylamino)phenyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazinecarbothioamide

HRID 514177Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:27]=[CH:26][C:18](/[CH:19]=[N:20]/[NH:21][C:22](SC)=[S:23])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[CH3:30][N:31]([CH3:39])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH2:38])[CH:33]=1>CN(C=O)C>[CH3:30][N:31]([CH3:39])[C:32]1[CH:33]=[C:34]([NH:38][C:22]([NH:21][N:20]=[CH:19][C:18]2[CH:17]=[CH:16][C:15]([C:12]3[N:13]=[CH:14][N:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:28])([F:1])[F:29])=[CH:9][CH:8]=4)[N:11]=3)=[CH:27][CH:26]=2)=[S:23])[CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a 50 mL round-bottomed flask containing (E)-methyl 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylidene)hydrazinecarbodithioate (250 mg, 0.571 mmol) in DMF (3 mL) was added N1,N1-dimethylbenzene-1,3-diamine (195 mg, 1.43 mmol). The contents were heated at 150° C. with stirring for 5 h before the solution was allowed to cool overnight. The mixture was filtered, and the filtrate was purified via RP-HPLC to afford the desired material (235 mg, 78%) as an off-white solid: mp 192-194° C.; 1H NMR (400 MHz, DMSO-d6) δ 11.82 (s, 1H), 10.04 (s, 1H), 9.41 (s, 1H), 8.19 (s, 1H), 8.16-7.99 (m, 6H), 7.61 (d, J=8.3 Hz, 2H), 7.16 (t, J=7.2 Hz, 1H), 7.01 (m, 1H), 6.87 (m, 1H), 6.58 (m, 1H), 2.88 (s, 6H); ESIMS m/z 526 ([M+H]+).

Workup

temperatureto cool overnight
filtrationThe mixture was filtered
customthe filtrate was purified via RP-HPLC

Sources & evidence

ORD record: ord-3201db77cd094cd9aea7df03b8bc1200
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107413B2

Reaction notes

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