1-Hydroxybenzotriazole → HCID 18331075, compound

HRID 2270055Notes

Reaction equation

HRID 2270055 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1)=[O:5].[CH2:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH2:18][CH3:19].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(N(CC)CC)C.ClCCl.O>[CH2:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:35]=[CH:34][C:30]([C:31]([NH:2][CH2:3][C:4]([C:6]3[CH:11]=[CH:10][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=3)=[O:5])=[O:32])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH2:18][CH3:19]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 20636134-(4-propoxyphenyl)benzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18613865193813-77-3

Product 1

HCID 18331075HCID 18331075, compoundYield 58.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-amino-4′-ethoxycarbonylacetophenone hydrochloride (700 mg), 4-(4-propoxyphenyl)benzoic acid (866 mg) and 1-hydroxybenzotriazole (456.5 mg) in triethylamine (0.47 ml) and dichloromethane (7 ml) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (WSC.HCl) (648 mg), and stirred for 5 hours at ambient temperature. To the reaction mixture was added water (100 ml), and extracted with dichloromethane. The organic layer was washed with 1N hydrochloric acid, water, saturated sodium hydrogen carbonate aqueous solution and brine. Then the organic layer was dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The solids were slurried in ethyl acetate, and collected by filtration to give 2-[4-(4-propoxyphenyl)benzoylamino]-4′-ethoxycarbonylacetophenone (746 mg).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with 1N hydrochloric acid, water, saturated sodium hydrogen carbonate aqueous solution and brine
  3. dry with materialThen the organic layer was dried over magnesium sulfate
  4. filtrationMagnesium sulfate was filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b1edf2820aa444a0b1f5d7cd3f20fc10
Source dataset
uspto-grants-2001_12
Patent number
US06331521B1

Reaction notes

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