Sulfuric Acid → HCID 86689231, compound

HRID 871020Notes

Reaction equation

HRID 871020 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=2)[C:3]=1[C:16]#[N:17].[OH:18]S(O)(=O)=O>>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=2)[C:3]=1[C:16]([NH2:17])=[O:18]

Participants

3

Reactant 2

HCID 1118Sulfuric Acid2×HCID 86689232HCID 86689232, compound

Product 1

HCID 86689231HCID 86689231, compoundYield 86%

Conditions

Temperature
65 °C

Procedure

A mixture of 5-amino-3-(3-nitrophenyl)isothiazole-4-carbonitrile (500 mg, 2.03 mmol) in 5 mL conc. H2SO4 was heated at 65° C. After 4 hours the mixture was slowly added to 75 mL ice water (including an additional reaction run on 0.50 mmol scale in 1.5 mL conc. H2SO4). The mixture was stirred for 10 min, and then the precipitate filtered and rinsed with water and 10% EtOAc/hexane to give the title compound as a light beige solid (572 mg, 86% combined yield).

Workup

  1. filtrationthe precipitate filtered
  2. washrinsed with water and 10% EtOAc/hexane

Sources & evidence

ORD record
ord-e724859f78244f11bf99c2904ee690cd
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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