Dimethyl Sulfoxide → HCID 86733465, compound

HRID 1077077Notes

Reaction equation

HRID 1077077 reaction equation
[Br-].[Br:2]CC1C=CC(C(OCC[N+](C)(C)C)=O)=CC=1.C(=O)(O)[O-].[Na+].CS(C)=O.[I-].[CH:29]([C:31]1[CH:45]=[CH:44][C:34]([C:35]([O:37][CH2:38][CH2:39][N+:40]([CH3:43])([CH3:42])[CH3:41])=[O:36])=[CH:33][CH:32]=1)=[O:30]>C(O)C.O>[Br-:2].[CH:29]([C:31]1[CH:45]=[CH:44][C:34]([C:35]([O:37][CH2:38][CH2:39][N+:40]([CH3:41])([CH3:42])[CH3:43])=[O:36])=[CH:33][CH:32]=1)=[O:30]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 215358682-{[4-(Bromomethyl)benzoyl]oxy}-N,N,N-trimethylethan-1-aminium bromideHCID 21535876HCID 21535876, compound

Product 1

HCID 86733465HCID 86733465, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

p-Bromomethyl benzoyl choline bromide (102 mg.) sodium bicarbonate (24.8 mg.) and dimethylsulfoxide (0.3 ml.) are heated in an oil bath at 125° for about 5 minutes until vigorous effervescence ceases. The solution is cooled giving a suspension which upon dilution with 2 ml. of water is dissolved. The addition of 5 ml. of absolute ethanol at room temperature yields a crystalline precipitate which is isolated by centrifugation. The solid is isolated, and dried in vacuo at 75° to yield a crisp glassy solid of hygroscopic character having spectral characteristics indicating the structure of p-formylbenzoyl choline iodide. In accordance with the foregoing procedure but starting with

Workup

  1. temperatureThe solution is cooled
  2. customgiving a suspension which upon dilution with 2 ml
  3. additionThe addition of 5 ml
  4. customis isolated by centrifugation
  5. customThe solid is isolated
  6. customdried in vacuo at 75°
  7. customto yield a crisp glassy solid of hygroscopic character

Sources & evidence

ORD record
ord-7c39a15e98dc4b5b93f4170cdccd7be7
Source dataset
uspto-grants-1976_05
Patent number
US03959351

Reaction notes

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