2-Aminothiophenol → HCID 178509260, compound

HRID 2261636Notes

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-32bfce7865c1495ea11e2ccabb3a1b31
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07847101B2

Reaction notes

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