Ethanol → 2-Methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-7-carbonitrile

HRID 2371048Notes

Reaction equation

HRID 2371048 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:10](=O)[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.CC1C=CC(S([CH2:22][N+:23]#[C-])(=O)=O)=CC=1.C(O)C.CC([O-])(C)C.[K+]>COCCOC>[CH3:1][C:2]1[S:3][C:4]2[CH:10]([C:22]#[N:23])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 161915Tosylmethyl isocyanideHCID 149133692-Methyl-5,6-dihydrobenzo[d]thiazol-7(4H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 672573622-Methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred and cooled solution of 5,6-dihydro-2-methylbenzo[d]thiazol-7(4H)-one (1.67 g, 10 mmol) and TOSMIC (2.5 g, 13 mmol) in a mixture of DME (25 mL) and absolute ethanol (25 mL) was added solid t-BuOK (2.8 g, 24 mmol) portionwise while keeping the reaction temperature between 5 and 10° C. The resulting mixture was stirred at room temperature for 30 minutes and at 30-45° C. for 30 minutes. The resulting suspension was cooled to room temperature. The precipitate (TosK) was removed by filtration and rinsed with DME. The combined DME solutions were concentrated under reduced pressure to give the crude product, which was purified by column chromatography.

Workup

  1. customthe reaction temperature between 5 and 10° C
  2. stirringThe resulting mixture was stirred at room temperature for 30 minutes and at 30-45° C. for 30 minutes
  3. customThe precipitate (TosK) was removed by filtration
  4. washrinsed with DME
  5. concentrationThe combined DME solutions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-33190a766f104e7a9c9532481b7f2d87
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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