5-Chloro-2-fluoroaniline → HCID 89876253, compound

HRID 1487036Notes

Reaction equation

HRID 1487036 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[CH2:2].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([F:21])=[C:18]([CH:20]=1)[NH2:19]>N1C=CC=CC=1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([F:21])=[C:18]([NH:19][S:9]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[CH2:2])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH:20]=1

Participants

4

Reactant 2

HCID 750155-Chloro-2-fluoroanilineHCID 9855777Styrene-4-sulfonyl chloride

Product 1

HCID 89876253HCID 89876253, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 4-vinylbenzene-1-sulfonyl chloride (950 mg, 4.69 mmol) in pyridine (8 mL) at 20° C. was added 5-chloro-2-fluoroaniline (682 mg, 4.69 mmol). The reaction mixture was stirred at 20° C. for 2 hours then evaporated in vacuo and redissolved in ethyl acetate. The organic phase was washed with saturated aqueous sodium carbonate (25 mL), dried using a hydrophobic frit and evaporated in vacuo to give the crude product as a yellow oil. The crude was purified by silica (Si) chromatography using a 0-25% ethyl acetate-cyclohexane gradient. The appropriate fractions were combined and evaporated in vacuo to give the required product, 822.7 mg as a white solid. LCMS [LCMS2] Rt 0.86 min, m/z (ES+) 312 (M+H).

Workup

  1. customthen evaporated in vacuo
  2. dissolutionredissolved in ethyl acetate
  3. washThe organic phase was washed with saturated aqueous sodium carbonate (25 mL)
  4. customdried
  5. customevaporated in vacuo
  6. customto give the crude product as a yellow oil
  7. customThe crude was purified by silica (Si) chromatography
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-decce6e40deb48b7a1b3e8c4e6e9c204
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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