Water → HCID 13473208, compound

HRID 2164616Notes

Reaction equation

HRID 2164616 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.O.S(=O)(=O)(O)[OH:21]>C(OCC)(=O)C>[OH:21][CH:2]([CH2:18][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:13])=[O:14])[S:11][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 13473207HCID 13473207, compound

Product 1

HCID 13473208HCID 13473208, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-(2,3-Epoxypropoxy)benzothiazole-2-sulfonamide (1.21 gm, 4.25 mmol) was dissolved in ethyl acetate (35 mL) and added to water (25 mL) containing concentrated sulfuric acid (2.5 mL). This two phase mixture was stirred at room temperature overnight and then was poured into water and repeatedly extracted with 5% methanol/ethyl acetate (V/V). The extracts were dried (Na2SO4) and evaporated. The residue (1.2 gm) was dissolved in methanol and allowed to sit overnight to give 1.0 gm of impure product. This material was purified by chromatography on silica gel, eluting with 1% methanol/ethyl acetate (V/V). The combined fractions containing product were evaporated and the residue was triturated with methanol to give material which was recrystallized from methanol/ethyl acetate (0.3 gm), m.p. 183°-185° C.

Workup

  1. extractionrepeatedly extracted with 5% methanol/ethyl acetate (V/V)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. customevaporated
  4. dissolutionThe residue (1.2 gm) was dissolved in methanol
  5. waitto sit overnight

Sources & evidence

ORD record
ord-a11c5d990bb14fe2a3a20f1418b599f1
Source dataset
uspto-grants-1985_03
Patent number
US04505923

Reaction notes

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