Hydrochloric Acid → 2-Thioxo-2,3-dihydro-1,3-benzoxazole-5-carbonitrile

HRID 1944696Notes

Reaction equation

HRID 1944696 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].C(O[C:14]([S-])=[S:15])C.[K+].Cl>N1C=CC=CC=1>[S:15]=[C:14]1[NH:1][C:2]2[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=2[O:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2712583-Amino-4-hydroxybenzonitrileHCID 2735045Potassium ethylxanthate

Product 1

HCID 105114792-Thioxo-2,3-dihydro-1,3-benzoxazole-5-carbonitrileYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-amino-4-hydroxybenzonitrile (50 mg, 0.37 mmol) and potassium O-ethyl-xanthate (65 mg, 0.41 mmol) in pyridine (0.75 mL) was heated at reflux for 2 h. After cooling, the mixture was poured into ice-water. Then concentrated hydrochloric acid (0.2 mL) was added. The solid was collected, washed with water and dried to give 2-thioxo-2,3-dihydrobenzooxazole-5-carbonitrile 30 mg (46%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. customThe solid was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-235cdd836f79439aae4999fb74ea8a4c
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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