Sodium Hydroxide → HCID 66585000, compound

HRID 1629988Notes

Reaction equation

HRID 1629988 reaction equation
[Cl:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]#[N:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+].[C:17]([O:21][C:22](=[O:27])[NH:23][CH2:24][CH2:25]Br)([CH3:20])([CH3:19])[CH3:18]>C(#N)C.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:17]([O:21][C:22](=[O:27])[NH:23][CH2:24][CH2:25][N:6]1[CH:5]=[C:4]([C:7]#[N:8])[C:3]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:2]1[Cl:1])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 66584727HCID 66584727, compound

Product 1

HCID 66585000HCID 66585000, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 51.6 g (254 mmol) of 5-chloro-4-phenyl-1H-pyrrole-3-carbonitrile in 400 ml of acetonitrile are added 20.4 g (509 mmol) of finely ground sodium hydroxide and 3.46 g (10.2 mmol) of tetrabutylammonium hydrogen sulfate, and the mixture is stirred vigorously for a few minutes, followed by adding 68.5 g (255 mmol) of tert-butyl(2-bromo-ethyl)carbamate (CAS 39684-80-5), and the mixture is then stirred for 4 hours at reflux. [After cooling, the solvent is evaporated off under reduced pressure, the residue is taken up in water and the product is extracted with ethyl acetate.] The organic phase is then dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give 67.9 g of tert-butyl{2-[2-chloro-4-cyano-3-phenyl-1H-pyrrol-1-yl]ethyl}carbamate in the form of a white powder after recrystallizing from acetonitrile, filtering off and drying.

Workup

  1. stirringthe mixture is then stirred for 4 hours
  2. temperatureat reflux
  3. temperature[After cooling
  4. customthe solvent is evaporated off under reduced pressure
  5. extractionthe product is extracted with ethyl acetate
  6. dry with material] The organic phase is then dried over sodium sulfate
  7. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-cce7ed050956451bb0e366b2ca4e8216
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

Loading…