Pivaloyl chloride → HCID 68871083, compound

HRID 1817902Notes

Reaction equation

HRID 1817902 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][C:12]1(O)[CH2:17][CH2:16][CH2:15][CH2:14]C1.[C:19](Cl)(=O)[C:20]([CH3:23])([CH3:22])[CH3:21].O.C1(C)C=CC(S(O)(=O)=[O:34])=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH2:10][C:11]3([OH:34])[CH2:12][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:19]([C:20]([CH3:23])([CH3:22])[CH3:21])=[N:1][C:2]=2[CH:7]=1

Participants

7

Reactant 4

HCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 68873408HCID 68873408, compound

Product 1

HCID 68871083HCID 68871083, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1-{[(2-amino-4-bromophenyl)amino]ethyl}cyclohexanol (Step B, 892 mg, 2.8 mmol) in toluene (15 mL) was added pivaloyl chloride (379 μL, 3.1 mmol) at room temperature. After stirring for 15 min, p-toluenesulfonic acid monohydrate (533 mg, 2.8 mmol) was added and the mixture was stirred under reflux for 17 h with Dean-Stark apparatus. Water (5 mL) and saturated sodium hydrogencarbonate aqueous solution were added and the mixture was extracted with ethyl acetate (15 mL×3). The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 then 4:1 as eluent) to afford the title compound (215 mg, 21%).

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux for 17 h with Dean-Stark apparatus
  3. extractionthe mixture was extracted with ethyl acetate (15 mL×3)
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-ffb79b9d0cb442e9a0bc713cd8cd6b8c
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

Loading…