Triethylamine → HCID 22287313, compound

HRID 1747931Notes

Reaction equation

HRID 1747931 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[I:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.CCN(CC)CC.[H-].[Na+]>C1COCC1.CN(C=O)C.O>[I:8][C:9]1[CH:15]=[CH:14][C:12]([N:13]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 108934-IodoanilineHCID 24758Sodium hydrideHCID 702254-Bromobutyryl chloride

Product 1

HCID 22287313HCID 22287313, compoundYield 39.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 4-bromobutanoyl chloride (15.0 g) in THF (dry) (150 mL) was added to a mixture of 4-iodoaniline (7.50 g) and Et3N (9.55 mL) in THF (dry) (150 mL) at 0° C. The mixture was stirred at 60° C. overnight. A mixture of NaH (60%, 4.11 g) in DMF (dry) (50 mL) was added to the mixture at 0° C. The mixture was stirred at 120° C. overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (3.84 g) as a white solid.

Workup

  1. additionwas added to the mixture at 0° C
  2. stirringThe mixture was stirred at 120° C. overnight
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-f7dea400b6b84b128900b954147346d7
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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