Phenoxyacetyl chloride → HCID 66847586, compound

HRID 517008Notes

Reaction equation

HRID 517008 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][S:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)(=[O:10])=[O:9])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[O:30]([CH2:37][C:38](Cl)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[O:30]([CH2:37][C:38]([N:1]1[CH2:2][CH2:3][CH:4]([NH:7][S:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)(=[O:10])=[O:9])[CH2:5][CH2:6]1)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 69703Phenoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 22721850HCID 22721850, compound

Product 1

HCID 66847586HCID 66847586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(Piperidin-4-yl)naphthalene-2-sulfonamide (50 mg, 0.17 moles) was dissolved in 10 mL DCM and to that di-isopropyl ethyl amine (0.1 mL, 0.34 moles) was added under nitrogen at 0° C. The reaction was allowed to stir for 10 min and phenoxy acetyl chloride (33 mg, 0.19 moles) was added at 0° C. and warmed room temperature and stirred for 3 h. After completion of the reaction as monitored by TLC, reaction was quenched with cold water and extracted with ethyl acetate (2×25 mL). The combined organic phase was washed with bicarbonate solution and brine and dried over sodium sulphate. The solvent was filtered and evaporated on rotavap to obtain a crude compound which was washed further with hexane to yield the title compound as a white solid.

Workup

  1. additionwas added under nitrogen at 0° C
  2. stirringstirred for 3 h
  3. customAfter completion of the reaction
  4. customas monitored by TLC, reaction
  5. customwas quenched with cold water
  6. extractionextracted with ethyl acetate (2×25 mL)
  7. washThe combined organic phase was washed with bicarbonate solution and brine
  8. dry with materialdried over sodium sulphate
  9. filtrationThe solvent was filtered
  10. customevaporated on rotavap
  11. customto obtain a crude compound which
  12. washwas washed further with hexane

Sources & evidence

ORD record
ord-15ca60cb90c142949e3af410c92a8817
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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