Propargylamine → N-propargyl-2,4-dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonamide

HRID 35498Notes

Reaction equation

HRID 35498 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])=[CH:4][C:3]=1[S:17](Cl)(=[O:19])=[O:18].[CH2:21]([NH2:24])[C:22]#[CH:23]>O1CCCC1>[CH2:21]([NH:24][S:17]([C:3]1[CH:4]=[C:5]([NH:9][S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])[C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])(=[O:19])=[O:18])[C:22]#[CH:23]

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 13300558HCID 13300558, compound

Product 1

HCID 13300566N-propargyl-2,4-dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonamideYield 66.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonyl chloride (1.5 g) was added to tetrahydrofuran (20 ml) containing propargylamine (0.5 g), and the resultant mixture was allowed to stand overnight at room temperature. Upon completion of the reaction, the mixture was concentrated. A 5% aqueous solution of hydrochloric acid was added to the residue, whereby an oily substance was deposited. The oily substance was extracted with chloroform and washed with a 5% aqueous solution of hydrochloric acid and water in order. The extract was concentrated and recrystallized from toluene to give 1.05 g of N-propargyl-2,4-dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonamide (Compound No. 35). M.P., 130.5°-132° C.

Workup

  1. customUpon completion of the reaction
  2. concentrationthe mixture was concentrated
  3. additionA 5% aqueous solution of hydrochloric acid was added to the residue, whereby an oily substance
  4. extractionThe oily substance was extracted with chloroform
  5. washwashed with a 5% aqueous solution of hydrochloric acid and water in order
  6. concentrationThe extract was concentrated
  7. customrecrystallized from toluene

Sources & evidence

ORD record
ord-1fa1d906d487453eaed9b357eea79a78
Source dataset
uspto-grants-1988_08
Patent number
US04767446

Reaction notes

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