Hydrochloric Acid → HCID 178522079, compound

HRID 572231Notes

Reaction equation

HRID 572231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].Cl.[NH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]1.CCN(CC)CC.Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]2)=[O:10])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 178479278HCID 178479278, compound

Product 1

HCID 178522079HCID 178522079, compoundYield 124.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-3-(trifluoromethyl)phenyl isocyanate (5 g, 22.6 mmol) in DMF (35 mL) were added trans-4-aminocyclohexanol hydrochloride (3.8 g, 24.8 mmol) and Et3N (3.5 mL, 24.8 mmol) at 0° C. The reaction mixture was warmed up to room temperature and stirred overnight. After adding 1N HCl (40 mL) and water, the resulting white precipitates were collected by suction filtration. The collected solid was thoroughly washed with water. White powers collected were dissolved in EtOH (200 mL) then aqueous 30% NaOH (25 mL) was added. The reaction mixture was refluxed overnight. EtOH was removed in vacuo. The precipitates were filtered and washed with water. Recrystallization from methanol afforded 9.5 g (42%) of the title compound as a white solid. Mp: 239.5-241.1° C. NMR (DMSO-d6): δ 8.79 (s, 1H), 8.06 (d, J=2 Hz, 1H), 7.55-7.47 (m, 2H), 6.20 (d, J 8 Hz, 1H), 4.54 (d, J=4 Hz, 1H), 3.45-3.34 (m, 2H), 1.86-1.75 (m, 4H), 1.28-1.11 (m, 4H).

Workup

  1. customthe resulting white precipitates
  2. filtrationwere collected by suction filtration
  3. washThe collected solid was thoroughly washed with water
  4. customWhite powers collected
  5. dissolutionwere dissolved in EtOH (200 mL)
  6. additionaqueous 30% NaOH (25 mL) was added
  7. temperatureThe reaction mixture was refluxed overnight
  8. customEtOH was removed in vacuo
  9. filtrationThe precipitates were filtered
  10. washwashed with water
  11. customRecrystallization from methanol

Sources & evidence

ORD record
ord-ce50989a130144ed8aaed7b10a4bb5ff
Source dataset
uspto-grants-2015_05
Patent number
US09029401B2

Reaction notes

Loading…