Allyl bromide → 6-Allyloxybenzothiazole-2-sulfonamide

HRID 2164612Notes

Reaction equation

HRID 2164612 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=1.[CH2:17](Br)[CH:18]=[CH2:19]>CO.CN(C)C=O>[CH2:19]([O:3][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=1)[CH:18]=[CH2:17]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 134732046-Allyloxybenzothiazole-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of sodium hydroxide (8.0 gm, 0.2 ml) in methanol (170 mL) was added dropwise to a solution of 6-hydroxybenzothiazole-2-sulfonamide (23.0 gm, 0.1 mol) and allyl bromide (10.0 mL, 0.12 mol) in dry dimethylformamide (100 mL). This mixture was stirred at room temperature for 16-20 hours and then poured into hydrochloric acid-ice water. The precipitate was collected by filtration, dissolved in ethyl acetate, washed with water, dried (Na2SO4) and evaporated. This residue was triturated with methylene chloride and the crystalline product was collected. (wt. 9.9 gm), m.p. 184°-187° C. A sample was recrystallized from 1,2-dichloroethane, m.p. 193°-195° C.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThis residue was triturated with methylene chloride
  7. customthe crystalline product was collected
  8. customA sample was recrystallized from 1,2-dichloroethane, m.p. 193°-195° C.

Sources & evidence

ORD record
ord-c55084d79b8145829a8dc5116d5ecfdb
Source dataset
uspto-grants-1985_03
Patent number
US04505923

Reaction notes

Loading…