Hydrochloric Acid → 6-methoxy-3H-benzooxazole-2-thione

HRID 70124Notes

Reaction equation

HRID 70124 reaction equation
[OH:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].O(CC)[C:12]([S-])=[S:13].[K+].Cl>N1C=CC=CC=1>[CH3:10][O:9][C:7]1[CH:6]=[CH:5][C:3]2[NH:4][C:12](=[S:13])[O:1][C:2]=2[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2735045Potassium ethylxanthateHCID 99421632-Amino-5-methoxyphenol

Product 1

HCID 106312506-methoxy-3H-benzooxazole-2-thione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Hydroxy-4-methoxyaniline (1.00 g, 7.19 mmol) and potassium O-ethyl xanthate (1.27 g, 7.91 mmol) were heated to reflux in pyridine (20 mL). After 2 h, the reaction mixture was allowed to cool to rt and was poured into a solution of conc. HCl (10 mL) in ice water (80 mL). The resulting white solid was collected by filtration, washed with water (3×), and dried in a vacuum oven. This gave 0.733 g (56%) of the desired product. LC-MS: RT=6.67 min., [M+H]+=182.1.

Workup

  1. filtrationThe resulting white solid was collected by filtration
  2. washwashed with water (3×)
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d26766dfaee04b5a8d381996468c45cb
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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