4-Chlorobenzenesulfonyl chloride → HCID 72497703, compound

HRID 1058665Notes

Reaction equation

HRID 1058665 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[C:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])[CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.CCCCCC>N1C=CC=CC=1.CCOC(C)=O>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[C:16]4[S:20][C:19](=[O:21])[NH:18][C:17]4=[O:22])[CH:10]=3)=[O:7])=[CH:23][CH:24]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8058HexaneHCID 86758834HCID 86758834, compound

Product 1

HCID 72497703HCID 72497703, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-Amino-N-[3-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-phenyl]-benzamide was dissolved in pyridine and treated with 4-chloro-benzenesulfonyl chloride in pyridine at 60° C. for 12 h. The solution-was cooled and diluted with EtOAc then washed with 10% aq. NaHSO4 followed by saturated aq. NaCl. The organic phase was separated, dried over Na2SO4 and concentrated under reduced pressure to give an oil. Trituration with hexane gave pure product.

Workup

  1. temperatureThe solution-was cooled
  2. washthen washed with 10% aq. NaHSO4
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil

Sources & evidence

ORD record
ord-bd53ab7bbe744974bbd5bedcadf0c5f8
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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