Isopropanol → HCID 86619830, compound

HRID 1426876Notes

Reaction equation

HRID 1426876 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[C:10]([N:12]=[C:13]=[S:14])[CH:9]=[C:8]([F:15])[CH:7]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH:23]([OH:26])([CH3:25])[CH3:24]>>[CH:23]([O:26][C:13](=[S:14])[NH:12][C:10]1[CH:9]=[C:8]([F:15])[CH:7]=[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:11]=1)([CH3:25])[CH3:24]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 8471TriethylamineHCID 86619831HCID 86619831, compound

Product 1

HCID 86619830HCID 86619830, compound

Conditions

Temperature
45 °C

Procedure

To a solution of 1-tert-butoxy-3-fluoro-5-isothiocyanatobenzene (460 g, 2.04 mol) in anhydrous isopropyl alcohol (3250 ml) was added triethylamine (315 g, 3.06 mol). The mixture was heated to reflux under N2 atmosphere for 16 h and the temperature was cooled to 40-50° C. After concentration, the resulting dark residue was diluted with n-heptane (1000 ml) and heated to 60° C. The mixture was slowly cooled to 25° C., at the same time seeding was added. A slurry was observed and stirred at 25° C. for 16 h before being cooled slowly to 0-10° C. within 2 h. After filtration and washing with n-heptane (200 ml), the collected solid was dried in oven under vacuum at 40-45° C. for 18 h to give (3-tert-Butoxy-5-fluoro-phenyl)-thiocarbamic acid O-isopropyl ester (453.1 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under N2 atmosphere for 16 h
  3. concentrationAfter concentration
  4. additionthe resulting dark residue was diluted with n-heptane (1000 ml)
  5. temperatureheated to 60° C
  6. temperatureThe mixture was slowly cooled to 25° C., at the same time seeding
  7. additionwas added
  8. temperaturebefore being cooled slowly to 0-10° C. within 2 h
  9. filtrationAfter filtration
  10. washwashing with n-heptane (200 ml)
  11. customthe collected solid was dried in oven under vacuum at 40-45° C. for 18 h

Sources & evidence

ORD record
ord-e0ef639d2ed14144b526427834bd4b0d
Source dataset
uspto-grants-2015_01
Patent number
US08933108B2

Reaction notes

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