Ammonium Acetate → HCID 15346450, compound

HRID 651412Notes

Reaction equation

HRID 651412 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:13][CH2:12][C:11](=O)[CH2:10][S:9]2)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+]>CO>[NH2:21][CH:11]1[CH2:12][S:13][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[S:9][CH2:10]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 21708421HCID 21708421, compound

Product 1

HCID 15346450HCID 15346450, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

22.4 g (0.1 mol) of 2-(4-methylphenyl)-1,3-dithian-5-one and 77.1 g (1.0 mol) of ammonium acetate were stirred in 250 ml of methanol with the addition of 37.5 g of molecular sieve (3 Å) for 30 minutes and 6.30 g (0.1 mol) of sodium cyanoborohydride were then added in portions at 20° C. The mixture was stirred at room temperature for 48 hours, diluted with methanol and filtered. The filtrate was concentrated and the residue was taken up in dilute hydrochloric acid/toluene. The hydrochloric acid phase was rendered basic with concentrated sodium hydroxide solution and extracted with ether. This gave 2.2 g of product as a colorless oil (9.8% of theory), which was reacted without further purification.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. extractionextracted with ether
  4. customThis gave 2.2 g of product as a colorless oil (9.8% of theory), which was reacted without further purification

Sources & evidence

ORD record
ord-651c2961f422433cb1b3931b09b89006
Source dataset
uspto-grants-2001_08
Patent number
US06281221B1

Reaction notes

Loading…