Sulfuric Acid → HCID 12953543, compound

HRID 2285767Notes

Reaction equation

HRID 2285767 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH:10]2[CH2:13][N:12]([CH:14]([CH3:16])[CH3:15])[CH2:11]2)[C:8]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:24].[OH-:28].[Na+]>>[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]([CH2:13][NH:12][CH:14]([CH3:16])[CH3:15])[CH2:11][O:28][C:8]2=[O:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

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

Product 1

HCID 12953543HCID 12953543, compound

Conditions

Temperature
130 °C

Procedure

α,α-Diphenyl-α-(1-isopropyl-3-azetidinyl)acetonitrile (142 g.; 0.49 mole) was added to 500 g. of 70% sulfuric acid at 90°-100° C. The temperature was raised to 130° C. for 48 hours. The cooled mixture was poured onto ice and the cold mixture made basic ty the addition of solid sodium hydroxide. The basic mixture was extracted with chloroform and the combined chloroform extracts dried over sodium sulfate and concentrated. The residual material was crystallized from an 80% isooctane-20% isopropyl ether solution. The 4,5-dihydro-3,3-diphenyl-4-isopropylaminomethylfuran-2(3H)one weighed 105 g. (69.3%) and melted at 78°-80° C.

Workup

  1. customat 90°-100° C
  2. additionThe cooled mixture was poured onto ice
  3. extractionThe basic mixture was extracted with chloroform
  4. dry with materialthe combined chloroform extracts dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residual material was crystallized from an 80% isooctane-20% isopropyl ether solution

Sources & evidence

ORD record
ord-50641655876241f685265d118d569e95
Source dataset
uspto-grants-1982_04
Patent number
US04324791

Reaction notes

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