Acetic Acid → HCID 19037059, compound

HRID 264848Notes

Reaction equation

HRID 264848 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:17][C:11]3([CH2:16][CH2:15][S:14][CH2:13][CH2:12]3)[CH:10]=C(C#N)[C:8]=2[CH:20]=1)([O-:3])=[O:2].[C:21]([OH:24])(=[O:23])[CH3:22].S(=O)(=O)(O)O>O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:17][C:11]3([CH2:16][CH2:15][S:14][CH2:13][CH2:12]3)[CH:10]=[C:22]([C:21]([OH:24])=[O:23])[C:8]=2[CH:20]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 19037054HCID 19037054, compound

Product 1

HCID 19037059HCID 19037059, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.13 g of 6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydrothiopyran]-4-carbonitrile, 10 ml of acetic acid, 5 ml of water and 5 ml of concentrated sulfuric acid was refluxed with heating for 2 hours. When the reaction mixture was poured into ice water, crystals were separated out. The crystals were dissolved into a sodium hydrogencarbonate solution and washed with methylene chloride. A water layer was acidified to be hydrochloric acid and extracted with methylene chloride. After an organic layer was washed with water and dried, the solvent was distilled. The resultant residue was crystallized by a mixed solvent of ethyl acetate and methanol to obtain 55 mg of 6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydrothiopyran]-4-carboxylic acid with a melting point of 259°-261° C.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 2 hours
  3. customwere separated out
  4. dissolutionThe crystals were dissolved into a sodium hydrogencarbonate solution
  5. washwashed with methylene chloride
  6. extractionextracted with methylene chloride
  7. washAfter an organic layer was washed with water
  8. customdried
  9. distillationthe solvent was distilled
  10. customThe resultant residue was crystallized by a mixed solvent of ethyl acetate and methanol

Sources & evidence

ORD record
ord-3add9a297c0042c59e4a9e405b75ba61
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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