2-Aminothiophenol → HCID 178509260, compound

HRID 1959797Notes

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

Reactant 3

HCID 87132-Aminothiophenol

HCID 14923Ammonium Hydroxide

HCID 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

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

Sources & evidence

ORD record: ord-00f1de1028ac434999294f3ff3b62662
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410272B2

Reaction notes

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