Hydrochloric Acid → HCID 68485825, compound

HRID 1966055Notes

Reaction equation

HRID 1966055 reaction equation
Cl.O[CH2:3][C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[N-]C(=O)C(C)(C)C.[NH2:22][C:23]([NH2:25])=[S:24]>O1CCOCC1.C(O)(C)C>[NH2:22][C:23]1[S:24][CH2:3][C:4]2[CH:9]=[C:8]([O:10][C:11]([F:12])([F:14])[F:13])[CH:7]=[CH:6][C:5]=2[N:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723790ThioureaHCID 178447229HCID 178447229, compound

Product 1

HCID 68485825HCID 68485825, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Concentrated HCl (4 ml) is added slowly to a solution of N-[2-hydroxymethyl-4-(trifluoromethoxy)phenyl]-pivaloylamide (0.35 g, 1.2 mmol) in dioxane (3 ml) and the resulting reaction mixture heated at 80° C. for 4 hours, then diluted with isopropanol (20 ml), and thiourea (0.14 g, 1.8 mmol) added and the mixture refluxed for 20 hours. The solvent is then evaporated under vacuum and the residue diluted with H2O, basified with 2 N NaOH, and extracted with CH2Cl2. The combined organic extracts are dried over Na2SO4 and concentrated under vacuum. The residue is purified by chromatography through silica, eluting with AcOEt/petroleum ether (1:1). The product is obtained as a yellow solid, with a yield of 84%. Recrystallisation from EtOH gives a solid with m.p. 115-118° C. 1H-NMR (CDCl3): 3.87 (s, 2H), 5.16 (br s, 2H), 6.97-7.11 (m, 3H). MS (ESI): m/z 249 (M+H+).

Workup

  1. customthe resulting reaction mixture
  2. additionadded
  3. temperaturethe mixture refluxed for 20 hours
  4. customThe solvent is then evaporated under vacuum
  5. additionthe residue diluted with H2O
  6. extractionextracted with CH2Cl2
  7. dry with materialThe combined organic extracts are dried over Na2SO4
  8. concentrationconcentrated under vacuum
  9. customThe residue is purified by chromatography through silica
  10. washeluting with AcOEt/petroleum ether (1:1)
  11. customThe product is obtained as a yellow solid, with a yield of 84%
  12. customRecrystallisation from EtOH
  13. customgives a solid with m.p. 115-118° C

Sources & evidence

ORD record
ord-9f3029ef94ed426ca961fe7a89e752f5
Source dataset
uspto-grants-2013_04
Patent number
US08420634B2

Reaction notes

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