Sulfuric Acid → HCID 54336563, compound

HRID 2163344Notes

Reaction equation

HRID 2163344 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][CH:17]=2)[C:14]#[N:15])[CH2:10]1)([CH3:8])[CH3:7].[OH-:28].[Na+]>>[C:16]1([C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH:11]2[CH2:12][N:9]([CH:6]([CH3:8])[CH3:7])[CH2:10]2)[C:14]([NH2:15])=[O:28])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 12822282HCID 12822282, compound

Product 1

HCID 54336563HCID 54336563, compound

Conditions

Temperature
70 °C

Procedure

To 80 ml. of concentrated sulfuric acid preheated to 70° C. was added 25 g. (0.86 mole) of α-(1-isopropyl-3-azetidinyl)-α,α-diphenylacetonitrile at a rate to maintain a temperature of 65°-75° C. The solution was heated at 70° C. for 18 hrs. and poured on ice. The mixture was made basic with 50% sodium hydroxide (while cooling with ice) and extracted with chloroform. The chloroform was dried (sodium sulfate) and concentrated. The residue was crystallized from ethyl acetate-ethanol to give 15.7 g. (59%) of product melting at 181°-184° C.

Workup

  1. custompreheated to 70° C.
  2. additionwas added 25 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 from ethyl acetate-ethanol
  8. customto give 15.7 g

Sources & evidence

ORD record
ord-72f4b0656ab345b9ad83e48a06ec0d19
Source dataset
uspto-grants-1979_01
Patent number
US04133881

Reaction notes

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