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Triethylamine → Methyl 4-[2-(3,4,5-trimethoxy-phenylcarbamoyl)-vinyl]-benzoate

HRID 1180802
Notes
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Reaction equation

HRID 1180802 reaction equation
N1(O[C:11]([CH:13]=[CH:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[O:12])C2C=CC=CC=2N=N1.CCN(CC)CC.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[NH2:37]>C(Cl)Cl>[CH3:44][O:43][C:39]1[CH:38]=[C:36]([NH:37][C:11]([CH:13]=[CH:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=2)=[O:12])[CH:35]=[C:34]([O:33][CH3:32])[C:40]=1[O:41][CH3:42]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 322853,4,5-TrimethoxyanilineHCID 72479810Methyl 4-[2-(benzotriazol-1-yloxycarbonyl)-vinyl]-benzoate

Product 1

HCID 68978918Methyl 4-[2-(3,4,5-trimethoxy-phenylcarbamoyl)-vinyl]-benzoateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension at room temperature of VIII (150 mg, 0.46 mmol) in anhydrous CH2Cl2 (10 ml) under nitrogen were added Et3N (194 μl, 1.39 mmol) and 3,4,5-trimethoxyaniline (94 mg, 0.51 mmol) or ArNH2(1.1–1.2 equiv.), respectively. The reaction mixture was heated to 60° C. After 20 h, the reaction mixture was concentrated, diluted with AcOEt, and successively washed with a saturated aqueous solution of NH4Cl, H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (AcOEt/CH2Cl2:15/85→20/80) to give the title product IXa (130 mg, 0.35 mmol, 75% yield) as a yellow solid. 1H NMR (300 MHz, acetone-d6) δ(ppm): 9.42 (bs, 1H), AB system (δA=8.09, δB=7.78, J=8.1 Hz, 4H), 7.75 (d, J=15.6 Hz, 1H), 7.21 (s, 2H), 7.00 (d, J=15.8 Hz, 1H), 3.94 (s, 3H), 3.85 (s, 6H), 3.73 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with AcOEt
  3. washsuccessively washed with a saturated aqueous solution of NH4Cl, H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on silica gel (AcOEt/CH2Cl2:15/85→20/80)

Sources & evidence

ORD record
ord-923b474ece4d4a9a8e4ab6c444ef5394
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07282608B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes