Benzoyl chloride → HCID 59350379, compound

HRID 2271390Notes

Reaction equation

HRID 2271390 reaction equation
[CH2:1]([NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)(=[O:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[H-].[Na+].[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([S:10]([N:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:12])=[O:11])[CH:18]=[CH:17][C:16]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 19681341HCID 19681341, compound

Product 1

HCID 59350379HCID 59350379, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of N-octyl-3,4-dimethoxybenzenesulfonamide (0.213 g, 0.646 mmol) in 2.00 mL of DMF, NaH (0.028 g, 0.711 mmol; 60% in oil dispersion) was added. After 30 min, benzoyl chloride (0.085 g, 0.731 mmol) was added. After a further 1 hr, the reaction mixture was diluted with 4:1 EtOAc/hexanes and washed with water (2×). The organic layer was dried over MgSO4 and concentrated in vacuo to yield a yellow solid. Purification by flash chromatography (28% ethyl acetate/hexanes) gave 0.040 g (18%) of the title compound as a clear oil.

Workup

  1. waitAfter a further 1 hr
  2. washwashed with water (2×)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto yield a yellow solid
  6. customPurification by flash chromatography (28% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6bebe50b230d4997a946c03f8126034e
Source dataset
uspto-grants-2015_09
Patent number
US09120744B2

Reaction notes

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