Water → HCID 86687425, compound

HRID 1473383Notes

Reaction equation

HRID 1473383 reaction equation
C([S:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([Cl:19])=[N:14][CH:13]=[C:12]2[F:20])C1C=CC=CC=1.ClN1C(C)(C)C(=[O:29])N(Cl)C1=O.[F:32][C:33]1[C:38]([F:39])=[C:37]([F:40])[C:36]([F:41])=[C:35]([F:42])[C:34]=1[OH:43].C(N(CC)CC)C.[OH2:51]>C(OCC)(=O)C.C(O)(=O)C.C(#N)C>[Cl:19][C:15]1[C:16]2[C:11](=[CH:10][C:9]([S:8]([O:43][C:34]3[C:33]([F:32])=[C:38]([F:39])[C:37]([F:40])=[C:36]([F:41])[C:35]=3[F:42])(=[O:29])=[O:51])=[CH:18][CH:17]=2)[C:12]([F:20])=[CH:13][N:14]=1

Participants

9

Reactant 5

HCID 962WaterHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 86687424HCID 86687424, compound

Product 1

HCID 86687425HCID 86687425, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A round-bottom flask was charged with 6-(benzylthio)-1-chloro-4-fluoroisoquinoline (0.088 g, 0.290 mmol), acetonitrile (2.73 ml), acetic acid (0.102 ml), and water (0.068 ml) to give a thin suspension. The flask was cooled in an ice-bath for 10 min, then 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.114 g, 0.579 mmol) was added in one portion, leading to a solution. The reaction was stirred for 30 minutes. 2,3,4,5,6-pentafluorophenol (0.061 ml, 0.579 mmol) was added followed by drop wise addition of triethylamine (0.101 ml, 0.724 mmol). The reaction was stirred for 30 minutes. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (12 g, gradient elution 0 to 25% EtOAc:Heptane) to afford perfluorophenyl 1-chloro-4-fluoroisoquinoline-6-sulfonate as a clear colorless oil. (ESI) 428.1 (M+H)+.

Workup

  1. customto give a thin suspension
  2. temperatureThe flask was cooled in an ice-bath for 10 min
  3. stirringThe reaction was stirred for 30 minutes
  4. washwashed with water
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe combined organic layers were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material was purified via column chromatography (12 g, gradient elution 0 to 25% EtOAc:Heptane)

Sources & evidence

ORD record
ord-e3f59fd36c204bef80428dc42c0f2b6c
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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