4-t-Butylbenzenesulfonyl chloride → HCID 178419148, compound

HRID 76007Notes

Reaction equation

HRID 76007 reaction equation
[BH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH2:9].[C:10]([C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11]>C(=O)=O>[BH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:20]([C:17]1[CH:18]=[CH:19][C:14]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 178419147HCID 178419147, compound

Product 1

HCID 178419148HCID 178419148, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

A 100 mL round-bottom flask was charged with 2-boranyl-4-chloro-phenylamine (1.1 g, 7.9 mmol) and 4-tert-butyl benzenesulfonyl chloride (2.7 g, 11.6 mmol). The flask was evacuated and purged with nitrogen, followed by the addition of pyridine (20 mL). The homogeneous light purple solution was stirred 4 hours, and then poured onto a rapidly stirring cold slurry of 6 M HCl (66 mL) (formed by placing the acidic solution in acetonic dry ice). The resultant precipitated sulfonamide was filtered, washed thoroughly with 10% HCl, and dried in vacuo to afford purplish solid. The crude product was purified by flash chromatograph to yield 1.3 g of product as colorless solid: MS (ES) M+H expected 336.5, found 336.5.

Workup

  1. customThe flask was evacuated
  2. custompurged with nitrogen
  3. additionfollowed by the addition of pyridine (20 mL)
  4. additionpoured onto
  5. stirringa rapidly stirring cold slurry of 6 M HCl (66 mL) (
  6. customformed
  7. customThe resultant precipitated sulfonamide
  8. filtrationwas filtered
  9. washwashed thoroughly with 10% HCl
  10. customdried in vacuo
  11. customto afford purplish solid
  12. customThe crude product was purified by flash chromatograph

Sources & evidence

ORD record
ord-9fac820784b4432cb58d392d44b0e5af
Source dataset
uspto-grants-2014_09
Patent number
US08835468B2

Reaction notes

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