Ethanolamine → HCID 15870204, compound

HRID 369400Notes

Reaction equation

HRID 369400 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]3[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=3)=[CH:10][C:9]=2[CH3:22])=[O:7])=[CH:4][CH:3]=1.[C:25](N1C=CN=C1)([N:27]1[CH:31]=[CH:30]N=C1)=[O:26].C(CN)[OH:38]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([NH:19][C:25]([NH:27][CH2:31][CH2:30][OH:38])=[O:26])=[CH:20][CH:21]=3)=[CH:10][C:9]=2[CH3:22])=[O:7])=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 682631,1'-CarbonyldiimidazoleHCID 15870200HCID 15870200, compound

Product 1

HCID 15870204HCID 15870204, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-{5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl}aniline (0.33 g, 0.98 mmol) and 1,1'-carbonyldiimidazole (0.4 g, 2.46 mmol) were dissolved in DMF, and the reaction mixture was stirred at room temperature for 1 h. Ethanolamine (0.3 ml, 4.91 mmol) was added and after 1.5 h the mixture was diluted with water. The product was extracted into ethyl acetate, and the organic layer was dried over MgSO4 and then concentrated under vacuum. Purification by flash chromatography (ethyl acetate), followed by recrystallization from hexane-chloroform gave 1-{4-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]phenyl}-3-(2-hydroxyethyl)urea (239 mg, 57%) as a solid, mp 209.6-210.2° C.

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. dry with materialthe organic layer was dried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customPurification by flash chromatography (ethyl acetate)
  5. customfollowed by recrystallization from hexane-chloroform

Sources & evidence

ORD record
ord-f46fd1069bd74cbeaf9a5c485f7bf74b
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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