Methanol → HCID 58183758, compound

HRID 2043812Notes

Reaction equation

HRID 2043812 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+].[C:20]1([N:26]([C:33]2[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CO>C(COC)OC>[C:20]1([N:26]([C:33]2[CH:40]=[CH:39][C:36]([CH2:37][C:10]#[N:11])=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

Product 1

HCID 58183758HCID 58183758, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
-55 °C

Procedure

A solution of 68.3 g (0.35 mol) of (p-toluenesulfonyl)methyl isocyanide (TOSMIC) in 300 ml of dimethoxyethane was added dropwise to a stirred suspension of 78 g (0.70 mol) of potassium tert-butoxide in 300 ml of dimethoxyethane at −30° C. under nitrogen. After the solution had been cooled to −55° C., a solution of 92 g (0.34 mol) of 4-(N,N-diphenylamino)benzaldehyde in 100 ml of dimethoxyethane was added dropwise. After stirring at −55° C. for 1 hour, methanol was added. The reaction solution was heated to boiling under reflux for 30 min. After the solution had been concentrated to dryness, the residue was taken up with 600 ml of water and 30 ml of acetic acid. The aqueous solution was extracted with methylene chloride. The combined organic phases were washed with a saturated sodium carbonate solution, dried over magnesium sulfate and concentrated to dryness. 75 g (79% of theory) of the desired nitrile were obtained.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 30 min
  3. concentrationAfter the solution had been concentrated to dryness
  4. extractionThe aqueous solution was extracted with methylene chloride
  5. washThe combined organic phases were washed with a saturated sodium carbonate solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fab837d8dd5a4a7abeb6d0b14fc37cc2
Source dataset
uspto-grants-2013_11
Patent number
US08586745B2

Reaction notes

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