1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 73053630, compound

HRID 870454Notes

Reaction equation

HRID 870454 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]([OH:19])=O)[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.[CH:38]1[CH:43]=[N:42][C:41]2[N:44](O)N=N[C:40]=2[CH:39]=1>C(Cl)Cl>[NH2:44][C:41]1[CH:40]=[C:39]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:17]([C:14]3[C:13](=[O:20])[N:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:11]([CH3:10])[C:15]=3[CH3:16])=[O:19])=[CH:3][C:4]=2[Cl:9])[CH:38]=[CH:43][N:42]=1

Participants

6

Reactant 4

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

Product 1

HCID 73053630HCID 73053630, compoundYield 277.8%

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-0bcd57a40a8e4169b9283fb7e2798af1
Source dataset
uspto-grants-2015_03
Patent number
US08969388B1

Reaction notes

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