Benzenesulfonyl chloride, 3,4-dichloro- → HCID 68572668, compound

HRID 747595Notes

Reaction equation

HRID 747595 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])[OH:10].[Cl:18][C:19]1[CH:20]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1[Cl:25]>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:26]([C:21]2[CH:22]=[CH:23][C:24]([Cl:25])=[C:19]([Cl:18])[CH:20]=2)(=[O:28])=[O:27])=[C:3]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[OH:10])[CH:4]=1

Participants

5

Reactant 2

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 11437092(2-Amino-5-chlorophenyl)(2-chlorophenyl)methanol

Product 1

HCID 68572668HCID 68572668, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 0.9 g of (2-amino-5-chlorophenyl)(2-chlorophenyl)methanol dissolved in 4 ml of pyridine is added 0.822 g of 3,4-dichlorobenzenesulfonyl chloride, and the mixture is left for 30 minutes at room temperature. The reaction medium is taken up in ethyl acetate and washed with water, and then with 1M hydrochloric acid solution. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with dichloromethane, to give 0.601 g of the expected product.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed on a column of silica gel
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-4019ba2b2718466c81232d7a2715e0ce
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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