Dicyclohexylamine → 1-Methyl-1H-pyrrole-2-carbonyl chloride

HRID 1072105Notes

Reaction equation

HRID 1072105 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=O.C1(NC2CCCCC2)CCCCC1.S(Cl)([Cl:25])=O>ClCCl.CCOCC>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([Cl:25])=[O:9]

Participants

6

Reactant 3

HCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 814531-Methyl-2-pyrrolecarboxylic acid

Product 1

HCID 27950921-Methyl-1H-pyrrole-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

500 mg (4 mmol) of 1-methyl-2-pyrrolecarboxylic acid in 5 ml of dichloromethane are introduced into a round-bottomed flask and under a nitrogen stream. There are added, dropwise, 790 μl (4 mmol) of dicyclohexylamine and, 30 minutes later, 290 μl (4 mmol) of thionyl chloride. The medium is stirred for 1 hour at room temperature and then heated for 2 hours at 50° C. The mixture is then diluted with ether and the precipitate is filtered off. The filtrate is evaporated off and a brown oil is obtained.

Workup

  1. additionThere are added
  2. temperatureheated for 2 hours at 50° C
  3. filtrationthe precipitate is filtered off
  4. customThe filtrate is evaporated off
  5. customa brown oil is obtained

Sources & evidence

ORD record
ord-25a2e754c5664df79d28be10f18eb4ec
Source dataset
uspto-grants-2005_06
Patent number
US06908939B2

Reaction notes

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