Chlorosuccinimide → HCID 86665286, compound

HRID 1970846Notes

Reaction equation

HRID 1970846 reaction equation
[F:1][C:2]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([S:21][CH3:22])[CH:15]=1)([C:10]([F:13])([F:12])[F:11])[C:3]([F:9])([F:8])[C:4]([F:7])([F:6])[F:5].[Cl:23]N1C(=O)CCC1=O>C(#N)C>[Cl:23][C:18]1[CH:19]=[C:14]([C:2]([F:1])([C:10]([F:11])([F:12])[F:13])[C:3]([F:9])([F:8])[C:4]([F:7])([F:6])[F:5])[CH:15]=[C:16]([S:21][CH3:22])[C:17]=1[NH2:20]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86665287HCID 86665287, compound

Product 1

HCID 86665286HCID 86665286, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-2-methylthio-phenylamine (Example 3.1) (21.85 g, 61.16 mmol) in acetonitrile (170 ml) was added N-chlorosuccinimide (“NCS”) (8.578 g, 64.22 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent:cyclohexane/ethyl acetate 4:1) to give 2-chloro-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-6-methylthiophenylamine (12.0 g, 50% yield). LC-MS (Method 2): RT=2.17, [M−H]−=392.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted twice with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (eluent:cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-1084e097d6524c35b5878e8cfe9b35a9
Source dataset
uspto-grants-2013_04
Patent number
US08431514B2

Reaction notes

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