1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 90025110, compound

HRID 520691Notes

Reaction equation

HRID 520691 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.[CH3:10][N:11]1[C:15]([CH3:16])=[C:14]([C:17](O)=[O:18])[C:13](=[O:20])[N:12]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl>[Cl:9][C:4]1[CH:3]=[C:2]([NH:1][C:17]([C:14]2[C:13](=[O:20])[N:12]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:11]([CH3:10])[C:15]=2[CH3:16])=[O:18])[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 775784-Amino-2-chlorophenolHCID 181649HOAtHCID 246564Antipyric acid

Product 1

HCID 90025110HCID 90025110, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of 4-amino-2-chlorophenol (4.0 g, 28.00 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (7.4 g, 30.11 mmol) in DCM (70 mL) were added EDCI (6.65 g, 30.11 mmol) and HOAT (0.76 g, 5.68 mmol). The mixture was stirred at 45° C. for 20 hours, then cooled to rt and filtered. The filter cake was washed with DCM (20 mL×3), and dried at 50° C. in a vacuum oven overnight to give the title product as a gray solid (7.1 g, 72.1%).

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered
  3. washThe filter cake was washed with DCM (20 mL×3)
  4. customdried at 50° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-81cb5f919aed4792b68ab76171a3bbf1
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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