Propargyl bromide → HCID 19753471, compound

HRID 483683Notes

Reaction equation

HRID 483683 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:15]([OH:17])=[O:16])[CH:11]=2)[CH:6]=1)(=[O:3])[CH3:2].Br[CH2:19][C:20]#[CH:21].C1COCC1>O>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:15]([CH2:21][C:20]#[CH:19])(=[O:17])=[O:16])[CH:11]=2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 19753470HCID 19753470, compound

Product 1

HCID 19753471HCID 19753471, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

160 g (0.64 mol) of 2-acetylaminonaphthalene-6-sulfinic acid were dissolved in 1000 ml of water at pH 6 and the solution was added dropwise to a solution of 84.1 g (0.7 mol) of 3-bromoprop-1-yne and 85 ml of THF. After the addition was complete, the reaction mixture was heated at from 40° to 60° C. until the reaction had ended (check by TLC). The precipitate formed was filtered off with suction at about 10° C., washed with water and dried, leaving 166.4 g of 2-acetylamino-6-(prop-1-yn-3-ylsulfonyl)naphthalene of the formula ##STR24## having a melting point of from 230° to 238° C.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated at from 40° to 60° C. until the reaction
  3. customThe precipitate formed
  4. filtrationwas filtered off with suction at about 10° C.
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-699ba929eaa340aa999ba1e6d56e41cc
Source dataset
uspto-grants-1993_07
Patent number
US05225595

Reaction notes

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