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Aniline → HCID 57824410, compound

HRID 1470818
Notes
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Reaction equation

HRID 1470818 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
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

HCID 57824410HCID 57824410, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 8028
Tetrahydrofuran
Solvent

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. 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 367 (M+H); mp 136-140° C.

Sources & evidence

ORD record
ord-06fc73ddc4884a65b30fb751d991efc6
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09006468B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes