Ammonia → HCID 178424903, compound

HRID 1749144Notes

Reaction equation

HRID 1749144 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([CH:11]1O[CH:14]=[N:13][CH:12]1S(C1C=CC(C)=CC=1)(=O)=O)[CH3:10].[NH3:26]>>[CH3:8][C:7]1[C:2]([CH3:1])=[C:3]([CH:9]([C:11]2[N:26]=[CH:14][NH:13][CH:12]=2)[CH3:10])[CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 71118471HCID 71118471, compound

Product 1

HCID 178424903HCID 178424903, compoundYield 89%

Conditions

Temperature
110 °C

Procedure

Compound of formula (23) (3.16 g, 8.84 mmol), prepared according to example 4, was dissolved in ammonia-saturated ethanol (40 ml, containing approximately 160 mmol ammonia) and heated to 110° C. for 3 h. The mixture was then evaporated to dryness, and the residue was mixed with an aqueous, saturated solution of NaHCO3 (20 ml). The mixture was extracted with toluene (2×20 ml), and the combined extracts were washed with water (2×20 ml). The combined extracts were then extracted with 10% aqueous HCl (3×20 ml), and the combined acidic extracts were basified with gaseous ammonia, and extracted with toluene (2×20 ml). The combined organic extracts were dried over Na2SO4, and concentrated under reduced pressure, to yield compound of formula (XX) (1.57 g, 89%).

Workup

  1. customThe mixture was then evaporated to dryness
  2. additionthe residue was mixed with an aqueous, saturated solution of NaHCO3 (20 ml)
  3. extractionThe mixture was extracted with toluene (2×20 ml)
  4. washthe combined extracts were washed with water (2×20 ml)
  5. extractionThe combined extracts were then extracted with 10% aqueous HCl (3×20 ml)
  6. extractionextracted with toluene (2×20 ml)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6ed30b4915814758a3bea42be0407de1
Source dataset
uspto-grants-2015_10
Patent number
US09156793B2

Reaction notes

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