Propargyl bromide → HCID 19753469, compound

HRID 483684

Reaction equation

HRID 483684 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Br[CH2:15][C:16]#[CH:17].C1COCC1>O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH2:17][C:16]#[CH:15])(=[O:13])=[O:12])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 4121504-(Acetylamino)benzenesulfinic acid

Product 1

HCID 19753469HCID 19753469, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

199 g (1.0 mol) of 4-acetylaminobenzenesulfinic acid were dissolved in 1000 ml of water at pH 6, the solution was added dropwise to a solution of 140 g (1.1 mol) of 3-bromoprop-1-yne and 200 ml of THF at from 40° to 50° C., and the mixture was maintained at that temperature until the reaction had ended (check by TLC). The precipitate formed was filtered off with suction at about 10° C., washed neutral with water and dried, leaving 205 g of 4-acetylamino-1-(prop-1-yn-3-ylsulfonyl)benzene (melting point 175°-179° C.). ##STR26##

Workup

  1. temperaturethe mixture was maintained at that temperature until the reaction
  2. customThe precipitate formed
  3. filtrationwas filtered off with suction at about 10° C.
  4. washwashed neutral with water
  5. customdried

Sources & evidence

ORD record
ord-a6575e51614c40819c6950e16f2f2b55
Source dataset
uspto-grants-1993_07
Patent number
US05225595

Linked notes

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