Sulfuric Acid → HCID 12822290, compound

HRID 1112275Notes

Reaction equation

HRID 1112275 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH:10]2[CH2:13][N:12]([CH3:14])[CH2:11]2)[C:8]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:22].[OH-:26].[Na+]>>[OH:26][CH2:13][CH:10]1[CH2:11][N:12]([CH3:14])[C:8](=[O:22])[C:7]1([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 12822283HCID 12822283, compound

Product 1

HCID 12822290HCID 12822290, compound

Procedure

Forty grams (0.153 mole) of α,α-diphenyl-α-(1-methyl-3-azetidinyl)acetonitrile was heated in 150 g. of 70% sulfuric acid solution for 48 hrs. at 130° C. The reaction mixture was poured onto ice and made basic with a 50% sodium hydroxide solution while cooling with the addition of more ice. This mixture was extracted with chloroform, combined extracts dried, filtered, and concentrated in vacuo. The residue was crystallized from toluene, weighed 34.5 g. and melted at 148°-150° C. Ten grams was recrystallized twice with toluene, weighed 7.5 g., and melted at 149°-151° C.

Workup

  1. customat 130° C
  2. additionThe reaction mixture was poured onto ice
  3. temperaturewhile cooling with the addition of more ice
  4. extractionThis mixture was extracted with chloroform
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from toluene
  9. customTen grams was recrystallized twice with toluene

Sources & evidence

ORD record
ord-6abd2a4cb9274f4c9c4ce2adcfbad13c
Source dataset
uspto-grants-1978_10
Patent number
US04120969

Reaction notes

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