1-Bromo-3-chloropropane → N-(3-chloropropyl)-N-(4-fluorophenyl)-4-methylbenzenesulfonamide

HRID 35299Notes

Reaction equation

HRID 35299 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][Cl:25]>CN(C)C=O>[Cl:25][CH2:24][CH2:23][CH2:22][N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 853960p-Toluenesulfonanilide, 4'-fluoro-

Product 1

HCID 19883457N-(3-chloropropyl)-N-(4-fluorophenyl)-4-methylbenzenesulfonamideYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 10.6 parts of N-(4-fluorophenyl)-4-methylbenzenesulfonamide in 68 parts of N,N-dimethylformamide were added portionwise 2.1 parts of a sodium hydride dispersion 50%: temp. rises to 35° C. After stirring for 20 minutes, the whole was cooled in an ice-bath (about 15° C.) and 12.6 parts of 1-bromo-3-chloropropane were added quickly. Stirring was continued first for 20 minutes at room temperature, then for 3 hours at 75° C. and further overnight at room temperature. The reaction mixture was poured onto ice-water and the product was extracted with methylbenzene. The extract was washed three times with water, dried, filtered and evaporated. The residue was crystallized from petroleumether. The product was filtered off and recrystallized from 2,2'-oxy bispropane, yielding 11.37 parts (83.2%) of N-(3-chloropropyl)-N-(4-fluorophenyl)-4-methylbenzenesulfonamide (intermediate 5).

Workup

  1. customrises to 35° C
  2. additionwere added quickly
  3. stirringStirring
  4. waitwas continued first for 20 minutes at room temperature
  5. waitfor 3 hours at 75° C.
  6. customfurther overnight
  7. customat room temperature
  8. additionThe reaction mixture was poured onto ice-water
  9. extractionthe product was extracted with methylbenzene
  10. washThe extract was washed three times with water
  11. customdried
  12. filtrationfiltered
  13. customevaporated
  14. customThe residue was crystallized from petroleumether
  15. filtrationThe product was filtered off
  16. customrecrystallized from 2,2'-oxy bispropane

Sources & evidence

ORD record
ord-0c7d8da2cb8e4b15bdbfbbe6bec36494
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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