Acetic Acid → HCID 86758909, compound

HRID 1264624Notes

Reaction equation

HRID 1264624 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[C:14](N1C=CN=C1)(N1C=CN=C1)=[S:15].C(O)(=O)C>C1(C)C=CC=CC=1>[S:15]=[C:14]1[NH:1][C:2]2[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=2[O:8]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 802641,1'-ThiocarbonyldiimidazoleHCID 1475136Methyl 2-(3-amino-4-hydroxyphenyl)acetate

Product 1

HCID 86758909HCID 86758909, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 3-amino-4-hydroxyphenylacetate (5.43 g, 0.03 mol) was suspended in toluene (60 ml) and 1,1′-thiocarbonyldiimidazole (5.34 g, 0.03 mol) was added. The resultant mixture was stirred for 30 minutes, then acetic acid (10 ml) was added and the mixture was heated under reflux for 3 hours. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was partitioned between water and ethyl acetate The organic extract was dried over magnesium sulfate, filtered and the filtrate was evaporated to give methyl (2,3-dihydro-2-thioxo-5-benzoxazolyl)acetate (6,2 g) as a light brown solid, m.p. 120-122° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customthe solvent was removed in vacuo
  4. customThe residue was partitioned between water and ethyl acetate The
  5. extractionorganic extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-dafd55e1150c4e78ae96a0dc99f9aa9b
Source dataset
uspto-grants-2003_04
Patent number
US06544989B2

Reaction notes

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