Triethylamine → tert-butyl 4-[N'-(2-methoxyphenyl)ureido]-3-methylphenylacetate

HRID 354364Notes

Reaction equation

HRID 354364 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[CH3:16].C(N(CC)CC)C.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]=[C:33]=[O:34]>C1COCC1>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:33](=[O:34])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])=[CH:4][C:3]=1[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 23512173Tert-butyl 4-amino-3-methylphenylacetate

Product 1

HCID 23512525tert-butyl 4-[N'-(2-methoxyphenyl)ureido]-3-methylphenylacetateYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-amino-3-methylphenylacetate (1.36 g, 6.15 mmol) and triethylamine (170 ml, 1.23 mmol) in THF (30 ml) was added 2-methoxyphenyl isocyanate (820 ml, 6.15 mmol), and the resulting mixture was stirred for 27 h. The mixture was concentrated to a small volume in vacuo, and hexane was added to the residue to give precipitate, which was collected by filtration to give tert-butyl 4-[N′-(2-methoxyphenyl)ureido]-3-methylphenylacetate (1.74 g, 76%) as a white crystallize material. mp 157-158° C.; 1H-NMR (CDCl3) δ1.46 (s, 9 H), 2.30 (s, 3 H), 3.50 (s, 2 H), 3.76 (s, 3 H), 6.43 (s, 1H), 6.83 (br d, J=8.4 Hz, 1 H), 6.95 (br d, J=8.0 Hz, 1 H), 6.98-4.99 (m, 2 H), 7.13 (brs, 1 H), 7.23 (br s, 1 H), 7.48 (d, J=8.8 Hz, 1 H), 8.14 (d, J=8.4 Hz, 1 H); MS (ESI) m/z 371 (M++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. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b2920a9081ba4e62add19c2f97cee011
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

Loading…