4-Chlorophenyl isothiocyanate → HCID 23139437, compound

HRID 540497Notes

Reaction equation

HRID 540497 reaction equation
[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH2:16])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[S:26])=[CH:20][CH:19]=1>C(Cl)Cl>[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:16][C:25]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)=[S:26])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 164804-Chlorophenyl isothiocyanateHCID 115727413-(4-Bromo-1-methyl-1H-pyrazol-5-yl)-4-methoxyaniline

Product 1

HCID 23139437HCID 23139437, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine (0.037 g, 0.13 mmol) was treated with 4-chlorophenyl isothiocyanate (0.024 g, 0.14 mmol, 1.05 equiv.) in CH2Cl2 (1 mL), in a similar manner as described in Example 1.10 to afford Compound 71 (0.048 g, 0.10 mmol, 80%) as a solid film. LCMS m/z (%)=451 (M+H79Br35Cl, 85), 453 (M+H81Br35Cl, 100), 455 (M+H81Br37Cl, 35). 1H NMR (400 MHz, CDCl3) δ: 8.00 (s, 1H), 7.85 (s, 1H), 7.53 (s, 1H), 7.48 (dd, J=2.7, 8.8 Hz, 1H), 7.37 (s, 4H), 7.30 (d, J=2.7 Hz, 1H), 7.08 (d, J=8.8 Hz, 1H), 3.87 (s, 3H), 3.75 (s, 3H).

Sources & evidence

ORD record
ord-cf2189333f854958ae622a10e82c9ab6
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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