Methanol → HCID 13473209, compound

HRID 2164617Notes

Reaction equation

HRID 2164617 reaction equation
[O:1]1[CH2:18][CH:2]1[CH2:3][O:4][C:5]1[CH:17]=[CH:16][C:8]2[N:9]=[C:10]([S:12]([NH2:15])(=[O:14])=[O:13])[S:11][C:7]=2[CH:6]=1.[CH3:19][OH:20]>>[CH3:19][O:20][CH2:18][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:17]=[CH:16][C:8]2[N:9]=[C:10]([S:12]([NH2:15])(=[O:14])=[O:13])[S:11][C:7]=2[CH:6]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 13473207HCID 13473207, compound

Product 1

HCID 13473209HCID 13473209, compound

Procedure

A solution of 6-(2,3-epoxypropoxy)benzothiazole-2-sulfonamide (2.15 gm, 7.5 mmol) in methanol (60 mL) containing five drops of concentrated sulfonic acid was stirred at room temperature, monitoring reaction progress by TLC until complete (3 hours). The reaction mixture was poured into ice water and the crude product extracted into ethyl acetate which was dried (Na2SO4) and evaporated. The residue was dissolved in a minimum amount of acetonitrile and diluted with chloroform. Upon standing overnight product crystallized (1.8 gm). After several recrystallizations from acetonitrile/chloroform pure product was obtained (1.2 gm), m.p. 153°-155° C.

Workup

  1. customreaction progress by TLC until complete (3 hours)
  2. extractionthe crude product extracted into ethyl acetate which
  3. dry with materialwas dried (Na2SO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in a minimum amount of acetonitrile
  6. additiondiluted with chloroform
  7. customproduct crystallized (1.8 gm)
  8. customAfter several recrystallizations from acetonitrile/chloroform pure product
  9. customwas obtained (1.2 gm), m.p. 153°-155° C.

Sources & evidence

ORD record
ord-6d3a82df3ef149729199e3011add91df
Source dataset
uspto-grants-1985_03
Patent number
US04505923

Reaction notes

Loading…