Potassium ethylxanthate → Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate

HRID 2041004Notes

Reaction equation

HRID 2041004 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].[C:13]([S-])(=[S:17])OCC.[K+]>N1C=CC=CC=1>[S:17]=[C:13]1[NH:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[O:12]1

Participants

4

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Product 1

HCID 45789990Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 4-amino-3-hydroxybenzoate (16.7 g, 100 mmol, Chemical Abstracts number 63435-16-5, available from Alfa Chemicals, 26 Parkridge Rd, Ward Hill, Mass. 01835-8099) and potassium O-ethyl carbonodithioate (20.8 g, 130 mmol) were combined in pyridine (100 mL) and refluxed for two hours. The reaction mixture was cooled to ambient temperature and the product was filtered, washed with water, and dried in a vacuum oven overnight at 45° C. to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.87 (d, 3 H) 7.34 (d, J=8.33 Hz, 1 H) 7.92 (d, J=1.59 Hz, 1 H) 7.97 (dd, J=12.69, 1.59 Hz, 1 H); MS (ESI−) m/z 207.9 (M−H)−.

Workup

  1. temperaturerefluxed for two hours
  2. filtrationthe product was filtered
  3. washwashed with water
  4. customdried in a vacuum oven overnight at 45° C.

Sources & evidence

ORD record
ord-37f4d9089eba4e0183a9f65f0d3a55b2
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

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