Hydrochloric Acid → 6-Allyloxybenzothiazole-2-sulfonamide

HRID 2164615Notes

Reaction equation

HRID 2164615 reaction equation
CN(C)C=[N:4][S:5]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[CH2:20])[CH:14]=[CH:13][C:11]=2[N:12]=1)(=[O:7])=[O:6].[OH-].[Na+].O.Cl>CO>[CH2:18]([O:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([S:5]([NH2:4])(=[O:7])=[O:6])[S:9][C:10]=2[CH:16]=1)[CH:19]=[CH2:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 53647804N,N-Dimethyl-N'-(6-allyloxybenzothiazole-2-sulfonyl)formamidine

Product 1

HCID 134732046-Allyloxybenzothiazole-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of product from Step B (0.45 gm, 1.4 mmol) in methanol (1.5 mL) was added to 2N sodium hydroxide (2 mL) and stirred at 40° C. for 1 hour. The reaction was poured into water, acidified (HCl), and the product extracted into ethyl acetate. The extract was dried (Na2SO4) and evaporated to give crude product. Upon trituration of this residue with methylene chloride, the product precipitated and was collected (0.18 gm) and shown to be identical with the product of Example 1.

Workup

  1. extractionthe product extracted into ethyl acetate
  2. dry with materialThe extract was dried (Na2SO4)
  3. customevaporated
  4. customto give crude product
  5. customUpon trituration of this residue with methylene chloride, the product precipitated
  6. customwas collected (0.18 gm)

Sources & evidence

ORD record
ord-5581e90325654ed8a600846d876b58ed
Source dataset
uspto-grants-1985_03
Patent number
US04505923

Reaction notes

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