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

HRID 1692028Notes

Reaction equation

HRID 1692028 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-390acafa8e4c4b30921b77e13cf7668d
Source dataset
uspto-grants-2012_04
Patent number
US08153813B2

Reaction notes

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