Water → HCID 67355942, compound

HRID 712938Notes

Reaction equation

HRID 712938 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][C:10]=1[I:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([NH2:24])([CH3:23])([CH3:22])[CH3:21].O>CCCCCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:24][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:11][C:10]=1[I:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 86623447HCID 86623447, compound

Product 1

HCID 67355942HCID 67355942, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
37.5 °C

Procedure

A 3-neck, 3 L, round-bottom flask was equipped with an over-head stirrer, thermometer, and a pressure-equalizing dropping-funnel was charged with the solution of 4-benzyloxy-3-iodo-benzenesulfonyl chloride. The flask immersed in a cold water bath (Tint=22° C.) and tert-butylamine (90.1 g, 0.710 mol, 2.1 eq) was added drop-wise (Tint no change). The resulting reaction mixture was stirred overnight at the ambient water-bath temperature. After 17 h, the reaction mixture was worked-up and the organic layer was separated and concentrated to approx. ⅓ (˜500 mL) of its original volume at which point the product started to precipitate. The reaction mixture was warmed to 35-40° C. at atmospheric pressure till the solids had re-dissolved. The solution was then allowed to cool, with gentle stirring, to room temperature. Within 2 days a white precipitate had formed. The suspension was stirred vigorously while hexane (1.5 L) was slowly added, then stirred overnight, and then cooled in an ice-bath for 1-2 h The precipitate was collected by filtration and washed with hexane, dried, first under suction to give 4-benzyloxy-N-tert-butyl-3-iodo-benzenesulfonamide (238, 94%).

Workup

  1. customA 3-neck, 3 L, round-bottom flask was equipped with an over-head stirrer
  2. customThe flask immersed in a cold water bath
  3. customThe resulting reaction mixture
  4. customthe organic layer was separated
  5. concentrationconcentrated to approx. ⅓ (˜500 mL) of its original volume at which point the product
  6. customto precipitate
  7. dissolutionhad re-dissolved
  8. temperatureto cool, with gentle stirring, to room temperature
  9. customWithin 2 days a white precipitate had formed
  10. additionwas slowly added
  11. temperaturecooled in an ice-bath for 1-2 h The precipitate
  12. filtrationwas collected by filtration
  13. washwashed with hexane
  14. customdried, first under suction

Sources & evidence

ORD record
ord-1acebcd9adae45e4b89a22020093e9bf
Source dataset
uspto-grants-2015_11
Patent number
US09181280B2

Reaction notes

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