2-Aminothiophenol → HCID 178509260, compound

HRID 57237Notes

Reaction equation

HRID 57237 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[NH2:9][C:10]1[C:14]([C:15]#N)=[CH:13][NH:12][N:11]=1.[OH-].[NH4+]>>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:15]1[C:14]1[C:10]([NH2:9])=[N:11][NH:12][CH:13]=1

Participants

4

Reactant 3

HCID 87132-AminothiophenolHCID 14923Ammonium HydroxideHCID 178510443HCID 178510443, compound

Product 1

HCID 178509260HCID 178509260, compoundYield 40.5%

Conditions

Temperature
200 °C

Procedure

A mixture of 2-aminobenzenethiol (100 mg, 0.8 mmol) and 3-aminopyrazole-4-carbonitrile (86 mg, 0.8 mmol) in 3 g of polyphosphoric acid was heated at 200° C. for 3 hours. The mixture was then poured into ice water and was neutralized with conc. Ammonium hydroxide solution. The resulting yellow solid was isolated by filtration and washed with cold water to yield the title compound (70 mg, 40%). MS (m/z, ES+): 217 (M+1, 100%); 1H NMR (300 MHz, ppm, DMSO-d6): δ 7.97 (d, 3J=7.8 Hz, 1H), 7.88 (s, 1H), 7.84 (d, 3J=8.0 Hz, 1H), 7.42 (m, 1H), 7.29 (m, 1H), 6.3 (br s, 2H).

Workup

  1. customThe resulting yellow solid was isolated by filtration
  2. washwashed with cold water

Sources & evidence

ORD record
ord-dd52b540650e4a0eb019559666de18f8
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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