Triethylamine → HCID 23511893, compound

HRID 350376Notes

Reaction equation

HRID 350376 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[N:17]=[C:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)[S:19][CH:20]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(N(CC)CC)C.[C:36]1([CH3:45])[C:37]([N:42]=[C:43]=[O:44])=[CH:38][CH:39]=[CH:40][CH:41]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[N:17]=[C:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:43]([NH:42][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[CH3:45])=[O:44])=[CH:26][CH:27]=2)[S:19][CH:20]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691942-Tolyl isocyanateHCID 23512000HCID 23512000, compound

Product 1

HCID 23511893HCID 23511893, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-methoxy-4-[2-(4-aminobenzyl)-4-thiazolyl]methoxybenzoate (87.8 mg, 0.220 mmol) in THF (2.0 mL) was added triethylamine (30.5 ul, 0.220 mmol) and o-tolyl isocyanate (30 μl), and the reaction mixture was stirred at room temp for 21 hr. The reaction mixture was poured into ice-water and the resulting precipitates filtered off. The filtrate was extracted with CHCl3, washed with H2O, and brine. The extract was dried over Na2SO4. The solvent was removed under a reduced pressure to afford 110.4 mg (94%) ethyl 3-methoxy4-[2-[4-[N′-(2-methylphenyl) ureido]benzyl]-4-thiazolyl]methoxybenzoate as a pale yellow crystalline powder. 1H-NMR (400 MHz, CDCl3) δ 1.38 (t, J=7.3 Hz, 3H), 2.28 (s, 3H), 3.92 (s, 3H), 4.28 (s, 2H), 4.35 (q, J=7.3 Hz, 2H), 5.29 (s, 2H), 6.20 (s, 1H), 6.47 (s, 1H), 6.97 (d, J=8.8 Hz, 1H), 7.20 (s, 1H), 7.24 (s, 2H), 7.27 (s, 2H), 7.33 (d, J=8.3 Hz, 2H), 7.49 (d, J=7.3 Hz, 1H), 7.56 (d, J=2.0 Hz, 1H), 7.63 (dd, J=2.0, 8.3 Hz, 1H); MS (FAB) m/z 532 (M++1).

Workup

  1. customthe resulting precipitates
  2. filtrationfiltered off
  3. extractionThe filtrate was extracted with CHCl3
  4. washwashed with H2O, and brine
  5. dry with materialThe extract was dried over Na2SO4
  6. customThe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-f9c5d89ca1a14d6ca865014ccb624ae4
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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