Aniline → HCID 57824410, compound

HRID 1424731Notes

Reaction equation

HRID 1424731 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[C:11]2=[O:26])=[CH:6][CH:5]=1)([O-])=O.NC1C=CC=CC=1.[N+](C1C=CC(N)=CC=1)([O-])=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1.C1COCC1>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][N:12]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]([F:23])([F:25])[F:24])=[CH:19][CH:20]=3)[C:11]2=[O:26])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 74754-NitroanilineHCID 94429TriphosgeneHCID 66968924HCID 66968924, compound

Product 1

HCID 57824410HCID 57824410, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Nitrophenyl)-2-(4-trifluoromethoxyphenyl)-2,4-dihydro-[1,2,4]triazol-3-one. The title compound was prepared according to the procedure in Henbach, DE 2724891 A1, 1978, with modifications to three steps: In the addition of the aniline, 4-nitroaniline was used instead of 3,5-dichloroaniline and dry THF was used as solvent instead of toluene. In the formation of the triazolinone ring, triphosgene (0.65 equiv) was used instead of phosgene: mp 136-140° C.; 1H NMR (300 MHz, CDCl3) δ 8.40 (d, J=8.8 Hz, 2H), 8.05 (d, J=8.8 Hz, 2H), 7.99 (s, 1H), 7.89 (d, J=9.3 Hz, 2H), 7.32 (d, J=9.3 Hz, 2H); ESIMS m/z 367 (M+H).

Sources & evidence

ORD record
ord-64e3405f8f924cd194317aa266954455
Source dataset
uspto-grants-2015_01
Patent number
US08927729B2

Reaction notes

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