Hydrochloric Acid → 5-Nitrobenzo[D]Oxazole-2-Thiol

HRID 1896761Notes

Reaction equation

HRID 1896761 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[C:12]([S-])(=[S:16])OCC.[K+].O.Cl>N1C=CC=CC=1>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:11][C:12](=[S:16])[NH:1][C:2]=2[CH:7]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2735045Potassium ethylxanthateHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 7862935-Nitrobenzo[D]Oxazole-2-ThiolYield 168.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

In accordance with well known procedures, (see Batista-Parra, A. et al. Heterocycles, 2003, 60, 1367), a suspension of 2-amino-4-nitrophenol (1.54 g, 10 mmol) and potassium O-ethyl carbonodithioate (1.68 g, 10.5 mmol) in dry pyridine (10 mL) was stirred at 120° C. for 6 h, and then at room temperature for 16 h. The solution was poured into water and aqueous hydrochloric acid was added. The resulting precipitate was collected by filtration, washed with dilute aqueous hydrochloric acid, followed by water and then dried in the vacuum oven to afford 3.3 g (84%) of the title compound.

Workup

  1. waitat room temperature for 16 h
  2. additionwas added
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with dilute aqueous hydrochloric acid
  5. customdried in the vacuum oven

Sources & evidence

ORD record
ord-6a0d43e41ac243ff8b3a1c41a3413629
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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