2-Tolyl isocyanate → t-Butyl 3-methoxy-4-o-tolylureidophenylacetate

HRID 381252Notes

Reaction equation

HRID 381252 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:18]1([CH3:27])[C:19]([N:24]=[C:25]=[O:26])=[CH:20][CH:21]=[CH:22][CH:23]=1>C(Cl)Cl>[CH3:17][O:16][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][C:25]([NH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH3:27])=[O:26]

Participants

4

Reactant 2

HCID 691942-Tolyl isocyanateHCID 22244730HCID 22244730, compound

Product 1

HCID 69645017t-Butyl 3-methoxy-4-o-tolylureidophenylacetateYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl 4-amino-3-methoxyphenylacetate (0.024 g, 0.10 mmol) in methylene chloride (2.0 mL) was added o-tolyl isocyanate (15 μL, 0.12 mmol). The reaction was stirred for 2 h then concentrated to afford t-Butyl 3-methoxy-4-o-tolylureidophenylacetate (0.036 g, 97%) as a tan foam: 1H NMR (CDCl3, 300 MHz, ppm) 8.05 (d, 7.9 Hz, 1H), 7.55 (d, 7.9 Hz, 1H), 7.45-7.05 (m, 5H), 6.78 (m, 2H), 3.73 (s, 3H), 3.48 (s, 2H), 2.23 (s, 3H), 1.44 (s, 9H).

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-c28acdebede5418f9411e9d2dec69e6e
Source dataset
uspto-grants-2001_10
Patent number
US06306840B1

Reaction notes

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