Dimethylformamide → HCID 21899461, compound

HRID 1986410Notes

Reaction equation

HRID 1986410 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=O)=[CH:4][C:3]=1[CH3:13].CN(C)C=O.C(Cl)(=O)C(Cl)=O.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[S:6][C:5]([C:7]([CH3:12])([CH3:11])[C:8]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:10])=[CH:4][C:3]=1[CH3:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 21899391HCID 21899391, compound

Product 1

HCID 21899461HCID 21899461, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the 2-(5-bromo-4-methyl-2-thienyl)-2-methylpropanoic acid in dichloromethane (10 ml) with a catalytic amount of dimethylformamide was added oxalyl chloride (0.30 ml, 0.34 mmol). The mixture was allowed to stir at ambient temperature for 2 hours. The solvent was evaporated and the crude acid chloride dried under vacuum. The crude acid chloride was dissolved in dichloromethane (10 ml) and cooled in an ice-bath. Pyrrolidine (1.2 ml, 14 mmol) was added and the mixture was allowed to stir for 30 minutes while being cooled in an ice-bath. The mixture was poured into ethyl acetate (25 ml) and then extracted with 1N hydrochloric acid. The organic layer was washed with a saturated brine solution, dried over magnesium sulfate and then evaporated to leave 1-[2-(5-bromo-4-methyl-2-thienyl)-2-methylpropanoyl]pyrrolidine as a red oil which was used in the next step without purification.

Workup

  1. customThe solvent was evaporated
  2. dry with materialthe crude acid chloride dried under vacuum
  3. dissolutionThe crude acid chloride was dissolved in dichloromethane (10 ml)
  4. temperaturecooled in an ice-bath
  5. stirringto stir for 30 minutes
  6. temperaturewhile being cooled in an ice-bath
  7. extractionextracted with 1N hydrochloric acid
  8. washThe organic layer was washed with a saturated brine solution
  9. dry with materialdried over magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-98450a5633b142cabe081261df386730
Source dataset
uspto-grants-2009_06
Patent number
US07547722B2

Reaction notes

Loading…