(R)-sec-butylamine → HCID 57527234, compound

HRID 1671791Notes

Reaction equation

HRID 1671791 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][C:12]#[N:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C@H:14]([NH2:18])([CH2:16][CH3:17])[CH3:15].CCOC(C)=O.CCCCCC>O1CCOCC1>[C@H:14]([NH:18][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][C:12]#[N:13])[CH:8]=[CH:7][C:5]=2[N:6]=1)([CH2:16][CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 2724537(R)-sec-butylamineHCID 21226206Ethyl acetate hexaneHCID 57527187HCID 57527187, compound

Product 1

HCID 57527234HCID 57527234, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-(2-bromobenzo[d]thiazol-6-yl)acetonitrile (2.00 g, 7.90 mmol) and (R)-sec-butylamine (4.0 mL, 39.4 mmol) in 1,4-dioxane (30 mL) was heated at 135° C. in a sealed bottle for 3.5 hr. The excess (R)-sec-butylamine and 1,4-Dioxane were removed under vacuum. The residue was diluted with AcOEt (150 mL), washed successively with saturated NaHCO3 solution (twice) and brine, and dried over anhydrous MgSO4. The title compound (1.35 g, 70% yield) was isolated as a light orange oil by ISCO (40% AcOEt/hexane).

Workup

  1. customThe excess (R)-sec-butylamine and 1,4-Dioxane were removed under vacuum
  2. additionThe residue was diluted with AcOEt (150 mL)
  3. washwashed successively with saturated NaHCO3 solution (twice) and brine
  4. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-266c6814a3c44e46aa60399606991cd6
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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