Ammonium Chloride → HCID 22393742, compound

HRID 1071628Notes

Reaction equation

HRID 1071628 reaction equation
CC(C)([O-])C.[K+].CC1C=CC(S([CH2:17][N+:18]#[C-])(=O)=O)=CC=1.[O:20]1[CH2:24][CH2:23][O:22][CH:21]1[C:25]1[CH:29]=[CH:28][S:27][C:26]=1[CH:30]=O.[Cl-].[NH4+]>CO.C1COCC1>[O:22]1[CH2:23][CH2:24][O:20][CH:21]1[C:25]1[CH:29]=[CH:28][S:27][C:26]=1[CH2:30][C:17]#[N:18]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 161915Tosylmethyl isocyanideHCID 115065723-(1,3-dioxolan-2-yl)thiophene-2-carbaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 22393742HCID 22393742, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

20 ml of a THF solution of 4.49 g (40.0 mmol) of potassium tert-butoxide was cooled to −45 to −30° C., and 20 ml of a THF solution of 3.90 g (20.0 mmol) of TOSmic and 20 ml of a THF solution of 3.68 g (20.0 mmol) of 3-(1,3-dioxolan-2-yl)-2-thiophenecarboaldehyde were successively added thereto. After 40 minutes, 60 ml of methanol was added at −15° C. After heating under reflux for 15 minutes, an aqueous saturated ammonium chloride was added, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give a crude product. The crude product was subjected to Cromatorex NH silica gel (ethyl acetate:hexane=1:4), to give 1.43 g (7.32 mmol, 36.6%) of the title compound as a yellow oil.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 15 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give a crude product

Sources & evidence

ORD record
ord-459621fcff294c72b0f35829aa2ccfcb
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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