Isopropanol → HCID 135974500, compound

HRID 734409Notes

Reaction equation

HRID 734409 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[S:10])[NH2:9])=[CH:4][C:3]=1[O:11][CH3:12].Cl[CH2:14][C:15](N(C)C)=O.[CH:20]([OH:23])([CH3:22])[CH3:21]>>[CH:20]([O:23][C:14]1[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:11][CH3:12])[CH:4]=2)[S:10][CH:15]=1)([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 758862-chloro-N,N-dimethylacetamideHCID 135741556HCID 135741556, compound

Product 1

HCID 135974500HCID 135974500, compoundYield 46%

Procedure

4-Hydroxy-3-methoxybenzenecarbothioamide (3.0 g, 16.37 mmol) (Example 35) and 2-chloro-N,N-dimethylacetamide were dissolved in isopropanol, and the mixture was heated at reflux for 12 h. The solvent was removed under reduced pressure. The residue was washed with water and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and the solvent was removed in vacuo. Purification via silica gel flash chromatography (ethyl acetate/hexane (v/v)=1:4) yielded a solid (1.99 g, 46%). 1H NMR (400 MHz, CDCl3) δ 1.42 (d, 6H), 3.91 (s, 3H), 4.64 (septet, 1H), 5.95 (s, 1H), 6.0 (br, 1H), 6.91 (d, 1H), 7.36 (d, 1H), 7.53 (s, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 12 h
  3. customThe solvent was removed under reduced pressure
  4. washThe residue was washed with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customPurification via silica gel flash chromatography (ethyl acetate/hexane (v/v)=1:4)

Sources & evidence

ORD record
ord-12ed633a09ba41c387558d1ad2356181
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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