Sulfuric Acid → HCID 12944282, compound

HRID 1277373Notes

Reaction equation

HRID 1277373 reaction equation
CN(CCCC(C#N)C1C=CC=CC=1C1C=CC=CC=1)C.S(=O)(=O)(O)O.[OH-].[Na+].[Cl-].[CH3:30][NH+:31]([CH2:33][CH2:34][CH2:35][CH:36]([C:49]([OH:51])=[O:50])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH3:32]>>[CH3:30][N:31]([CH2:33][CH2:34][CH2:35][CH:36]([C:49]([OH:51])=[O:50])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[CH3:32]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 12944273HCID 12944273, compoundHCID 23453890HCID 23453890, compound

Product 1

HCID 12944282HCID 12944282, compound

Conditions

Temperature
5 °C

Procedure

A solution of 6.0 g. of N,N-dimethyl-4-cyano-4-(1,1'-biphenyl-2-yl)butylamine in 65 ml. of 90% sulfuric acid was heated on a steam bath for eight hours. After cooling the reaction mixture to 5° C. and making it alkaline by the addition of 10% sodium hydroxide, the product was extracted therefrom intodiethyl ether. The ethereal extracts were washed with water and dried. Excess hydrogen chloride was bubbled into the ethereal solution, whereupona precipitate formed and was collected by filtration. Crystallization of the precipitate from ethanol afforded 2.9 g. of N,N-dimethyl-4-hydroxycarbonyl-4-(1,1'-biphenyl-2-yl)butylaminium chloride. M.P. 192°-194° C.

Workup

  1. extractionthe product was extracted
  2. washThe ethereal extracts were washed with water
  3. customdried
  4. customExcess hydrogen chloride was bubbled into the ethereal solution
  5. customwhereupona precipitate formed
  6. filtrationwas collected by filtration
  7. customCrystallization of the precipitate from ethanol
  8. customafforded 2.9 g

Sources & evidence

ORD record
ord-c554316e08ac4e9981a17eeb0db5a188
Source dataset
uspto-grants-1981_07
Patent number
US04277471

Reaction notes

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