Triethylamine → HCID 23511759, compound

HRID 350429Notes

Reaction equation

HRID 350429 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[O:16][CH3:17].C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]=[C:34]=[O:35]>C1COCC1>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34](=[O:35])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])=[CH:4][C:3]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 22244730HCID 22244730, compound

Product 1

HCID 23511759HCID 23511759, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-amino-3-methoxylphenylacetate (1.41 g, 5.94 mmol) and triethylamine (165 ml, 1.19 mmol) in THF (20 ml) was added 2-methoxyphenyl isocyanate (790 ml, 5.94 mmol), and the resulting mixture was stirred for 4 days. The mixture was concentrated to a small volume in vacuo, and hexane was added to the residue to give precipitate, which was collected to give tert-butyl 4-[N′-(2-methoxyphenyl)ureido]-3-methoxylphenylacetate (2.06 g, 90%) as a white crystalline material. mp 132–134° C.; 1H-NMR (CDCl3) δ 1.46 (s, 9 H), 3.50 (s, 2 H), 3.87 (s, 3 H), 3.88 (s, 3 H), 6.84 (s, 1 H), 6.87–6.90 (m, 2 H), 6.98–7.03 (m, 2 H), 7.12 (s, 1 H), 7.16 (s, 1 H), 8.06 (d, J=8.4 Hz, 1 H), 8.13 (dd, J=7.2, 2.0 Hz, 1 H); MS (ESI) m/z 387 (N++H).

Workup

  1. concentrationThe mixture was concentrated to a small volume in vacuo, and hexane
  2. additionwas added to the residue
  3. customto give precipitate, which
  4. customwas collected

Sources & evidence

ORD record
ord-17e2d6d7f6324f11a599f3013b4202f3
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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