Benzenesulfonamide → N-(Benzenesulfonyl)-2-chloro-N-(prop-2-en-1-yl)benzamide

HRID 236684Notes

Reaction equation

HRID 236684 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8])=[O:5].[C:20]1(S(N)(=O)=O)[CH:25]=CC=C[CH:21]=1.ClC1C=CC=CC=1C(Cl)=O.[H-].[Na+].C(Br)C=C>O1CCCC1>[CH2:25]([N:6]([C:4](=[O:5])[C:3]1[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=1[Cl:1])[S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH:20]=[CH2:21]

Participants

7

Reactant 5

HCID 7370BenzenesulfonamideHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 691102-Chlorobenzoyl chlorideHCID 706235HCID 706235, compound

Product 1

HCID 23331012N-(Benzenesulfonyl)-2-chloro-N-(prop-2-en-1-yl)benzamideYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.0 g (0.01 mole) of N-2-chlorobenzoyl benzenesulfonamide prepared from benzenesulfonamide and 2-chlorobenzoyl chloride was added to 0.58 g (0.012 mole) of 50% sodium hydride in 15 ml of dry tetrahydrofuran. After stirring for 30 minutes at room temperature, 1.48 g (0.012 mole) of allyl bromide was added. Then the mixture was reacted for 2 hours under the same conditions. The tetrahydrofuran was distilled off under reduced pressure, and cold water was added. The resulting oil layer was extracted with benzene. The benzene layer was separated, dried over anhydrous magnesium sulfate, and concentrated to afford a white solid. Recrystallization from methanol afforded compound No. 27 in Table 2 in a yield of 35%.

Workup

  1. customThen the mixture was reacted for 2 hours under the same conditions
  2. distillationThe tetrahydrofuran was distilled off under reduced pressure, and cold water
  3. additionwas added
  4. extractionThe resulting oil layer was extracted with benzene
  5. customThe benzene layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto afford a white solid
  9. customRecrystallization from methanol afforded compound No

Sources & evidence

ORD record
ord-fe4ac7e130064b6e90b03fba885665e8
Source dataset
uspto-grants-1979_06
Patent number
US04157257

Reaction notes

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