Dimethylformamide → HCID 21283484, compound

HRID 2232371Notes

Reaction equation

HRID 2232371 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:16]=[CH:15][C:7]2[S:8][C:9]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:10][C:6]=2[CH:5]=1.[N-:17]=[N+:18]=[N-:19].[Na+].CN(C=O)C>O>[N:17]([CH2:2][CH2:3][C:4]1[CH:16]=[CH:15][C:7]2[S:8][C:9]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:10][C:6]=2[CH:5]=1)=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 13922876HCID 13922876, compound

Product 1

HCID 21283484HCID 21283484, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen, a solution of 5-(2-bromoethyl)-2-sulfamoylbenzo[b]thiophene (1.2 g, 0.0037 mol), NaN3 (0.6 g, 0.0092 mol) and DMF (25 ml) was heated at 100° C. After 18 hours, the solution was cooled, poured into H2O, and filtered to yield 0.8 g of product. The filtrate was extracted with ethyl acetate (2x). The organic layers were dried, filtered and concentrated to dryness to yield an additional 0.4 g of product (75%).

Workup

  1. temperaturethe solution was cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a0c26f7ec72d4e56b494addd5801fea2
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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