Ammonium Acetate → 3-Amino-5-phenylthiopyran

HRID 277155Notes

Reaction equation

HRID 277155 reaction equation
[C:1]1([C:7]2[CH2:8][C:9](=O)[CH2:10][S:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:20].[Na+]>CO>[NH2:20][C:9]1[CH2:10][S:11][CH:12]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 12521138HCID 12521138, compound

Product 1

HCID 695963343-Amino-5-phenylthiopyranYield 20.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was prepared as shown in Scheme 25. Thus, to 0.96 g (5 mmol) of 5-phenyl-3-thiopyranone (P. T. Lansbury, et al., J. Am. Chem. Soc. 1970, 92, 5649) in 50 mL of anhydrous methanol was added 7.7 g (100 mmol) of ammonium acetate and 6.5 g of 3A molecular sieves. After stirring 30 minutes at room temperature, 1.25 g (20 mmol) of sodium cyanoborohydride was added portionwise. After stirring 16 hours, the mixture was gravity filtered, and the methanol was evaporated under vacuum. The residue was partitioned between ice/HCl and ether. The acidic aqueous phase was extracted twice more with ether, then it was made basic with ice and 50% NaOH aqueous. The mixture was extracted with CH2Cl2, dried (MgSO4), and evaporated to give 0.19 g (20%) of the title compound. GC/MS showed 100% purity with a molecular ion of 193.

Workup

  1. customThis compound was prepared
  2. stirringAfter stirring 16 hours
  3. filtrationfiltered
  4. customthe methanol was evaporated under vacuum
  5. customThe residue was partitioned between ice/HCl and ether
  6. extractionThe acidic aqueous phase was extracted twice more with ether
  7. extractionThe mixture was extracted with CH2Cl2
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-f9fd1191a52848599be1ea4aa9199410
Source dataset
uspto-grants-2002_03
Patent number
US06355660B1

Reaction notes

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