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Dicyclohexylcarbodiimide → Ethyl 4-[(5,5-dimethyl-8-(carbethoxymethyl)-5,6-dihydronaphthalen-2-yl)azo]benzoate

HRID 635598
Notes
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Reaction equation

HRID 635598 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:11][CH2:10][C:9](O)([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]2[CH:7]=[C:6]([N:19]=[N:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=3)[CH:5]=[CH:4][C:3]1=2.C1CCC(N=C=NC2CCCCC2)CC1>C1C=CC=CC=1.Cl[Cu]>[CH3:32][C:2]1([CH3:1])[CH2:11][CH:10]=[C:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]2[CH:7]=[C:6]([N:19]=[N:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:30][CH:31]=3)[CH:5]=[CH:4][C:3]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 22571557(+/-) Ethyl 4-[(5,5-dimethyl-8-hydroxy-8-carbethoxymethy5,6,7,8-tetrahydronaphth-2-yl)azo]benzoate2×

Product 1

HCID 22571504Ethyl 4-[(5,5-dimethyl-8-(carbethoxymethyl)-5,6-dihydronaphthalen-2-yl)azo]benzoate

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalyst
HCID 241
Benzene
Solvent

Procedure

A solution of (+/−) ethyl 4-[(5,5-dimethyl-8-hydroxy-8-carbethoxymethyl-5,6,7,8-tetrahydronaphth-2-yl)azo]benzoate (Compound D1, 108 mg, 0.25 mmol), DCC (55.9 mg, 0.271 mmol) and CuCl (36.6 mg, 0.37 mmol) in 8 ml of dry benzene was heated under reflux for 7 days. After cooling to room temperature, the solids were filtered out and the solution was extracted with ethyl acetate. The combined organic layer was washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure, the crude material was purified by flash chromatography (silicagel, 10 % ethyl acetate in hexane) to afford the pure title compounds as red oils.

Workup

  1. temperatureunder reflux for 7 days
  2. filtrationthe solids were filtered out
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe crude material was purified by flash chromatography (silicagel, 10 % ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0ad19b709f334ef38c943b532da14551
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06187933B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes