Triethylamine → HCID 57588317, compound

HRID 1782191Notes

Reaction equation

HRID 1782191 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:20])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=[CH:7][CH:8]=1)#[CH:2].C(N(CC)CC)C.[Cl:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:30]=1[C:31](Cl)=[N:32][OH:33]>O1CCCC1.C(OCC)(=O)C>[Cl:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:30]=1[C:31]1[CH:2]=[C:1]([C:3]2[CH:4]=[C:5]([NH:9][C:10](=[O:20])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:6]=[CH:7][CH:8]=2)[O:33][N:32]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28001642,6-DichlorobenzaldchloroximeHCID 47451721HCID 47451721, compound

Product 1

HCID 57588317HCID 57588317, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-(3-ethynylphenylamino)-2-oxoethylcarbamate (1.6 g, 5.83 mmol) was dissolved in anhydrous tetrahydrofuran (25 mL) and treated with triethylamine (0.82 g, 8.1 mmol) and then 2,6-dichloro-N-hydroxybenzimidoyl chloride (1.4 g, 6.3 mmol). After stirring 15 min at room temperature the mixture was heated at reflux for 4 h. The mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give tert-butyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)-2-oxoethylcarbamate. 1H NMR (CDCl3): 8.51 (br s, 1H), 8.01 (s, 1H), 7.51-7.45 (m, 2H), 7.40-7.28 (m, 4H), 6.63 (m, 1H), 5.28 (br s, 2H), 3.95 (d, 2H), 1.45 ppm (s, 9H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff60e3aa8a074314b81765d581055ed8
Source dataset
uspto-grants-2009_03
Patent number
US07498353B2

Reaction notes

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