Aniline → HCID 13498651, compound

HRID 1828880Notes

Reaction equation

HRID 1828880 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:15]([S:19](Cl)(=[O:21])=[O:20])[CH2:16][CH2:17][CH3:18]>C(Cl)Cl>[CH2:15]([S:19]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:21])=[O:20])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 754301-Butanesulfonyl chloride

Product 1

HCID 13498651HCID 13498651, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

9.9 ml of aniline (10.1 g, 108.4 mmol) and 15 ml of triethylamine (11.0 g, 108.4 mmol) were dissolved at 50° C. in 108 ml of methylene chloride. Again at 50° C. 14.1 ml of n-butanesulfonyl chloride (17.0 g, 108.4 mmol) were added dropwise to this solution over the course of 1 h. After 15 minutes of stirring at 50° C. the reaction mixture was extracted twice with 100 ml of water. The resultant crude product in solution in 150 ml of methylene chloride was extracted with 150 ml of 1 N NaOH. The aqueous phase was adjusted to a pH of 1–2 using concentrated HCl and was extracted twice with 100 ml of methylene chloride. Drying over magnesium sulphate and removal of the methylene chloride by distillation gave 17.0 g of the target compound, whose constitution was verified by NMR spectroscopy.

Workup

  1. customAgain at 50° C
  2. extractionwas extracted twice with 100 ml of water
  3. extractionThe resultant crude product in solution in 150 ml of methylene chloride was extracted with 150 ml of 1 N NaOH
  4. extractionwas extracted twice with 100 ml of methylene chloride
  5. dry with materialDrying over magnesium sulphate and removal of the methylene chloride by distillation

Sources & evidence

ORD record
ord-e0f606deeb2f41e29ee2556f6edab074
Source dataset
uspto-grants-2006_06
Patent number
US07060817B2

Reaction notes

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