1,2-Dichloroethane → N-(2,4-dichlorobenzoyl)-4-(tert-butyldimethylsilyloxy)-phenylsulfonamide

HRID 351123Notes

Reaction equation

HRID 351123 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[O:12]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)[Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(Cl)CCl>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:29][S:26]([C:23]1[CH:22]=[CH:21][C:20]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])=[CH:25][CH:24]=1)(=[O:27])=[O:28])=[O:6]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 57872,4-Dichlorobenzoic AcidHCID 210912414-(Tert-butyl-dimethylsiloxy)phenylsulfonamide

Product 1

HCID 21091248N-(2,4-dichlorobenzoyl)-4-(tert-butyldimethylsilyloxy)-phenylsulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2,4-dichlorobenzoic acid (1.25 eq) in dry dichloromethane (10 mL/mmol), 4-(tert-butyl-dimethylsiloxy)phenylsulfonamide (1.0 eq) is added in one portion followed by EDC (1.25–1.5 eq) and finally, NN-dimethyl-4-aminopyridine (1.2 equiv). The mixture is vigorously stirred under nitrogen for 16 hr, concentrated under reduced pressure, and the residue partitioned between ethyl acetate and water. The organic layer is washed with 1N hydrochloric acid (4 times, 20 mL/mmol), then the combined aqueous phases extracted with ethyl acetate (twice, 20 mL/mmol). The combined organic layers are finally washed with water and saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by silica gel chromatography or crystallization if necessary or desired. ESI-MS m/e 458.0 (M+−H; 460.0 (M++H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic layer is washed with 1N hydrochloric acid (4 times, 20 mL/mmol)
  4. extractionthe combined aqueous phases extracted with ethyl acetate (twice, 20 mL/mmol)
  5. washThe combined organic layers are finally washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel chromatography or crystallization if necessary or

Sources & evidence

ORD record
ord-86f591923262408ab9c4114230275de2
Source dataset
uspto-grants-2007_02
Patent number
US07183320B2

Reaction notes

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