Water → HCID 57586710, compound

HRID 1097737Notes

Reaction equation

HRID 1097737 reaction equation
Cl[C:2]1[CH:11]=[C:10]([S:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH2:20]>C(O)(C(F)(F)F)=O.Cl>[F:19][C:16]1[CH:17]=[CH:18][C:13]([S:12][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2](=[O:20])[CH:11]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 962WaterHCID 57586726HCID 57586726, compound

Product 1

HCID 57586710HCID 57586710, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-chloro-4-(4-fluoro-phenylsulfanyl)-quinoline (145 mg, 0.50 mmol) in TFA (2 mL) and HCl (6 N, 2 mL) was heated under microwave radiation at 120° C. for 20 min. After cooling down, 20 mL of water was added. The precipitate was collected by filtration and washed with water for several times. The product was air dried (115 mg, 85%) and was pure enough without further purification. Note: the solubility of the product in organic solvent is very poor. 1H NMR (500 MHz, DMSO-d6) δ 11.6 (bs, 1H), 7.82 (d, J=8.0 Hz, 1H), 7.71 (m, 2H), 7.56 (t, J=8.0 Hz, 1H), 7.43 (m, 3H), 7.33 (d, J=8.0 Hz, 1H), 7.23 (t, J=8.0 Hz, 1H), 5.56 (s, 1H); LCMS (EI) m/z 272.0 (M+), 273.0.

Workup

  1. temperatureAfter cooling down
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water for several times
  4. customdried (115 mg, 85%)
  5. customwas pure enough without further purification

Sources & evidence

ORD record
ord-1747f9156e944807aff786ee378b4cf1
Source dataset
uspto-grants-2012_03
Patent number
US08143276B2

Reaction notes

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