Water → HCID 15508927, compound

HRID 478129Notes

Reaction equation

HRID 478129 reaction equation
BrC(CC)C(O)=O.O.[C:9]1([S:15]([CH:18]([CH2:22][CH3:23])[C:19](O)=[O:20])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.S(Cl)([Cl:26])=O>C(OCC)(=O)C.CN(C=O)C>[C:9]1([S:15]([CH:18]([CH2:22][CH3:23])[C:19]([Cl:26])=[O:20])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 66552-Bromobutanoic acidHCID 24386Thionyl ChlorideHCID 15112216HCID 15112216, compound

Product 1

HCID 15508927HCID 15508927, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromobutyric acid, (200 g, 1.2 mol), sodium benzenesulfinate,(236 g, 1.44 mol) and water(1000 mL) were heated to 80° C. After about 1 hour the clear solution had turned cloudy and an oil had precipitated out. After heating at 80° C. for a total of 2 hours the mixture was cooled with good stirring. The oil solidifies and the crystals were filtered off, washed with water and air-dried. Yield 162.5 g. 2-Phenylsulfonylbutyric acid (47.8 g, 0.21 mol) was suspended/dissolved in ethyl acetate (400 mL) to which was added DMF (0.5 mL), thionyl chloride (76 mL, 1.05 mol) and the mixture heated to 70° C. for 2 hrs. After this period the solution was cooled, concentrated under reduced pressure and co-evaporated with ethyl acetate (×1). The resulting pale yellow oil was used as such in the preparation of inventive coupler IC-1.

Workup

  1. customan oil had precipitated out
  2. temperaturewas cooled with good stirring
  3. filtrationthe crystals were filtered off
  4. washwashed with water
  5. customair-dried
  6. temperaturethe mixture heated to 70° C. for 2 hrs
  7. temperatureAfter this period the solution was cooled
  8. concentrationconcentrated under reduced pressure and co-evaporated with ethyl acetate (×1)
  9. customsuch in the preparation of inventive coupler IC-1

Sources & evidence

ORD record
ord-8d43e649d43f456abf8ea6bfbfe110d7
Source dataset
uspto-grants-2003_11
Patent number
US06641990B1

Reaction notes

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