Water → HCID 67599453, compound

HRID 1417324Notes

Reaction equation

HRID 1417324 reaction equation
Cl.[C:2]1([C:8]([C:10]2[CH:21]=[CH:20][C:13]([O:14][CH:15](N)[CH2:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.O.CCCCCC.[N:40]1C=CC=CC=1>C(N(CC)CC)C.ClCCl>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:40][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:13]2[CH:20]=[CH:21][C:10]([C:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:9])=[CH:11][CH:12]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8058HexaneHCID 86753758HCID 86753758, compound

Product 1

HCID 67599453HCID 67599453, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2.0 g of 4-[(4-phenylcarbonylphenoxy]butaneamine hydrochloride (example 62) in a mixture of 40 ml of pyridine and 3 ml of triethylamine is added 2.0 g of 4-bromobenzenesulfonyl chloride. The reaction mixture is stirred at room temperature for 18 hours, heated on the steam bath for one hour, and then added to 250 ml of water. Cooling at 0° C. gives an oil which is dissolved in 100 ml of dichloromethane. Addition of 150 ml of hexane is followed by concentration to turbidity (steam bath), and the mixture cooled at -10° C. An oily solid is precipitated and fine white crystals are produced in the supernatant solvent. These are carefully separated and dried; m.p. 71°-73° C.; recovery, 0.2 g.

Workup

  1. temperatureheated on the steam bath for one hour
  2. temperatureCooling at 0° C.
  3. customgives an oil which
  4. concentrationis followed by concentration to turbidity (steam bath)
  5. temperaturethe mixture cooled at -10° C
  6. customAn oily solid is precipitated
  7. customfine white crystals are produced in the supernatant solvent
  8. customThese are carefully separated
  9. customdried

Sources & evidence

ORD record
ord-1b4fe80e4cb54574ad7a04645c861ee2
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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