1,1'-Carbonyldiimidazole → HCID 59185796, compound

HRID 1951244Notes

Reaction equation

HRID 1951244 reaction equation
[C:1]([C:4]1[C:5]([CH3:13])=[C:6]([C:10]([OH:12])=O)[NH:7][C:8]=1[CH3:9])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[Cl:27][CH2:28][CH2:29][NH2:30]>CN(C=O)C>[Cl:27][CH2:28][CH2:29][NH:30][C:10]([C:6]1[NH:7][C:8]([CH3:9])=[C:4]([C:1](=[O:3])[CH3:2])[C:5]=1[CH3:13])=[O:12]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2232774-Acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acidHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 59185796HCID 59185796, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Acetyl-3,5-dimethylpyrrole carboxylic acid (15.731 g, 86.82 mmol), was taken up in anhydrous DMF (40 mL) and cooled to 0° C. Carbonyldiimidazole (14.512 g, 86.82 mmol) was added to this slurry and stirred until the evolution of gas ceased and a clear solution formed. 2-Chloroethyl amine hydrochloride (10.574 g, 91.16 mmol) was added in one portion. The reaction mixture was left to stir overnight at room temperature. The reaction mixture was extracted in water (50 mL) from DCM (4×20 mL). The aqueous layer (containing precipitate) was filtered off and washed with cold water. The white solid was found to be the target compound. (10.316 g, 42.51 mmol, 49% yield).

Workup

  1. customa clear solution formed
  2. waitThe reaction mixture was left
  3. stirringto stir overnight at room temperature
  4. extractionThe reaction mixture was extracted in water (50 mL) from DCM (4×20 mL)
  5. additionThe aqueous layer (containing precipitate)
  6. filtrationwas filtered off
  7. washwashed with cold water

Sources & evidence

ORD record
ord-3c3d03cac4ce40b299c1ad1af8f25964
Source dataset
uspto-grants-2013_03
Patent number
US08404692B2

Reaction notes

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