Sulfuric Acid → alpha-(1-Isopropyl-3-azetidinyl)-alpha-phenyl-alpha-(2-pyridyl)acetamide

HRID 2163343Notes

Reaction equation

HRID 2163343 reaction equation
S(=O)(=O)(O)O.[CH:6]([N:9]1[CH2:12][CH:11]([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:14]#[N:15])[CH2:10]1)([CH3:8])[CH3:7].[OH-:28].[Na+]>>[CH:6]([N:9]1[CH2:12][CH:11]([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:14]([NH2:15])=[O:28])[CH2:10]1)([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 53832876HCID 53832876, compound

Product 1

HCID 54326586alpha-(1-Isopropyl-3-azetidinyl)-alpha-phenyl-alpha-(2-pyridyl)acetamide

Conditions

Temperature
70 °C

Procedure

To 80 ml. of concentrated sulfuric acid preheated to 70° C. was added 15 g. (0.052 mole) of α-(1-isopropyl-3-azetidinyl)-α-phenyl-α-(2-pyridyl)acetonitrile at a rate to maintain 65°-70° C. The solution was heated to 70° C. for 18 hrs. and poured on ice. The mixture was made basic with 50% sodium hydroxide (with ice cooling and extracted with chloroform. The chloroform was dried (sodium sulfate) and concentrated. The residue was crystallized twice from ethyl acetate-isopropyl ether. Yield 6 g. (37%), m.p. 140°-141° C.

Workup

  1. custompreheated to 70° C.
  2. additionwas added 15 g
  3. additionand poured on ice
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform was dried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe residue was crystallized twice from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-61dc00c9602848589bb604884d18eca5
Source dataset
uspto-grants-1979_01
Patent number
US04133881

Reaction notes

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