Phenylhydrazine hydrochloride → 1-[2-chloro-3-(trifluoromethyl)phenyl]-5-(2,3-dihydro-1H-inden-1-yl)-1H-1,2,4-triazole

HRID 2232973Notes

Reaction equation

HRID 2232973 reaction equation
Cl.[Cl:2][C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:13][NH2:14].Cl.[C:16]1(NN)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(C(N)=O)C2C(=CC=CC=2)CC1.C1(C)C=CC=CC=1CC(N)=O.[CH:47]([NH:49][C:50](=O)[CH2:51][C:52]1C=CC=C[CH:53]=1)=O>>[Cl:2][C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][C:4]=1[N:13]1[C:50]([CH:51]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:53][CH2:52]2)=[N:49][CH:47]=[N:14]1

Participants

6

Reactant 5

HCID 60962Phenylhydrazine hydrochlorideHCID 1180992,3-dihydro-1H-indene-1-carboxamideHCID 3268658N-formyl-2-phenylacetamideHCID 171457242-(2-Methylphenyl)acetamideHCID 68708803(2-Chloro-3-(trifluoromethyl)phenyl)hydrazine hydrochloride

Product 1

HCID 166781951-[2-chloro-3-(trifluoromethyl)phenyl]-5-(2,3-dihydro-1H-inden-1-yl)-1H-1,2,4-triazole

Procedure

The title compound was prepared using the procedure as described in Example 80 substituting 2-chloro-3-trifluoromethylphenylhydrazine hydrochloride for phenylhydrazine hydrochloride and substituting N-formyl-2,3-dihydro-1H-indene-1-carboxamide (prepared using the procedure as described in Example 76A, substituting from indan-1-carboxamide [Seidl Tetrahedron 1964, 20, 633] for 2-o-tolylacetamide) for N-formylphenylacetamide. The residue was purified by flash chromatography (40% ethyl acetate/hexanes) to provide the title compound. MS (ESI) m/e: 364 (M+H)+; 1H NMR (DMSO-d6) δ 2.05-2.45 (m, 2H), 2.8-3.05 (m, 2H), 4.29-4.35 (t, 1H), 6.95-7.05 (bs, 1H), 7.03-7.1 (t, 1H), 7.1-7.21 (t, 1H), 7.2-7.3 (d, 1H), 7.78-7.82 (t, 2H), 8.0-8.01 (bs, 0.5H), 8.18 (s, 1H), 8.22 (bs, 0.5H); Anal. calcd. for C, 59.43; H, 3.60; N, 11.55. Found C, 59.20; H, 3.34; N, 11.48

Workup

  1. customThe title compound was prepared
  2. customprepared
  3. customThe residue was purified by flash chromatography (40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-64a7e22ef0964347af69f3d7424b8a93
Source dataset
uspto-grants-2010_05
Patent number
US07709469B2

Reaction notes

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