Methyl iodide → Methyl 2-[2-(2-methylpropyl)benzothiazol-5-yl]propionate

HRID 48172Notes

Reaction equation

HRID 48172 reaction equation
[CH:1]([N-]C(C)C)(C)C.[Li+].C(C1C=CC=CC=1)C.CCCCCCC.[CH3:24][O:25][C:26](=[O:41])[CH2:27][C:28]1[CH:29]=[CH:30][C:31]2[S:35][C:34]([CH2:36][CH:37]([CH3:39])[CH3:38])=[N:33][C:32]=2[CH:40]=1.CI>O1CCCC1>[CH3:39][CH:37]([CH3:38])[CH2:36][C:34]1[S:35][C:31]2[CH:30]=[CH:29][C:28]([CH:27]([CH3:1])[C:26]([O:25][CH3:24])=[O:41])=[CH:40][C:32]=2[N:33]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 22742086Methyl[2-(2-methylpropyl)benzothiazol-5-yl]acetateHCID 86759364Ethylbenzene heptane

Product 1

HCID 22742088Methyl 2-[2-(2-methylpropyl)benzothiazol-5-yl]propionateYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium diisopropylamide (2.0M solution in tetrahydrofran/ethylbenzene/heptane, 2.09 ml, 0.0042 mol) was added, dropwise, to a solution of methyl[2-(2-methylpropyl)benzothiazol-5-yl]acetate (1.1 g, 0.0042 mol) in tetrahydrofuran (27 ml) at −78° C. under a nitrogen atmosphere and the mixture was stirred at below −60° C. for 1 hour. Methyl iodide (2.29 ml, 0.037 mol) was added, dropwise, and the mixture was stirred at below −60° C. for a further 1 hour. The cooling bath was removed and the mixture was allowed to warm to room temperature over a period of 1 hour. The mixture was diluted with water, acidified with 2M aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo to give methyl 2-[2-(2-methylpropyl)benzothiazol-5-yl]propionate (1.15 g) which was used without further purification in the next step.

Workup

  1. customThe cooling bath was removed
  2. additionThe mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-344c3d98059b458586760dfa59c4605a
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

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