Triethylamine → HCID 178472357, compound

HRID 1893352Notes

Reaction equation

HRID 1893352 reaction equation
Cl[C:2](=[N:14][OH:15])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.Cl.[C:17](=[NH:22])(OCC)[CH3:18].C(N(CC)CC)C>ClCCl>[CH2:12]([O:11][C:9]([C@H:6]1[CH2:7][CH2:8][C@H:3]([C:2]2[N:22]=[C:17]([CH3:18])[O:15][N:14]=2)[CH2:4][CH2:5]1)=[O:10])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 178472360HCID 178472360, compound

Product 1

HCID 178472357HCID 178472357, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of cis/trans-ethyl 4-(chloro(hydroxyimino)methyl)cyclohexanecarboxylate (1.85 g, 7.92 mmol) and ethyl acetimidate hydrochloride (1.96 g, 15.8 mmol) in dichloromethane (40 ml) was added triethylamine (2.2 ml, 16 mmol) at 0-5° C. The cooling bath was removed 15 minutes after completed addition, and stirring for 18 h at room temperature was followed by heating at reflux for 4 h. The reaction mixture was washed with one 50-ml portion of 1 M aqueous hydrochloric acid solution. The aqueous layer was extracted with two 50-ml portions of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/tert-butyl methyl ether as eluent gave the title compound (1.05 g, 56%) as colorless oil. MS m/e: 239 ([M+H]+)

Workup

  1. customThe cooling bath was removed 15 minutes
  2. additionaddition
  3. temperatureby heating
  4. temperatureat reflux for 4 h
  5. washThe reaction mixture was washed with one 50-ml portion of 1 M aqueous hydrochloric acid solution
  6. extractionThe aqueous layer was extracted with two 50-ml portions of dichloromethane
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-826722e220c04a6cbb6bf71486c5addf
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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