Ammonia → HCID 15035999, compound

HRID 1656462Notes

Reaction equation

HRID 1656462 reaction equation
[NH3:1].[O:2]1[CH:8]2[CH:3]1[C:4]([CH3:27])([CH3:26])[O:5][C:6]1[CH:12]=[CH:11][C:10]([S:13]([C:16]([F:25])([F:24])[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])(=[O:15])=[O:14])=[CH:9][C:7]=12.O>C(O)C>[NH2:1][C@@H:8]1[C:7]2[CH:9]=[C:10]([S:13]([C:16]([F:25])([F:24])[C:17]([F:22])([F:23])[C:18]([F:19])([F:20])[F:21])(=[O:14])=[O:15])[CH:11]=[CH:12][C:6]=2[O:5][C:4]([CH3:26])([CH3:27])[C@H:3]1[OH:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 15035998HCID 15035998, compound

Product 1

HCID 15035999HCID 15035999, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30 ml of 28% v/v aqueous ammonia were added to a solution of 1.086 g of 3,4-epoxy-6-heptafluoropropylsulfonyl-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (prepared as described in Preparation 3) in 30 ml of ethanol, and the resulting mixture was allowed to stand at room temperature for 3 days. At the end of this time, the reaction mixture was poured into water and extracted with methylene chloride. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and then the resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the eluent. The fractions containing the desired compound were then recrystallized from a mixture of ethyl acetate and hexane, to afford 0.796 g of the title compound, melting at 176°-177° C.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of cyclohexane and ethyl acetate as the eluent
  7. additionThe fractions containing the desired compound
  8. customwere then recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b68f382e0f084aeda8af5b8b76ea3e47
Source dataset
uspto-grants-1993_10
Patent number
US05254578

Reaction notes

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