Ethyl 2-chloro-5-isocyanatobenzoate → Ethyl 2-chloro-5-{3-[2-(ethoxycarbonyl)-1-methylpropenyl]ureido}-benzoate

HRID 845986Notes

Reaction equation

HRID 845986 reaction equation
[NH2:1]/[C:2](/[CH3:10])=[C:3](/[CH3:9])\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:11][C:12]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(OCC)C>[Cl:11][C:12]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:1][C:2]([CH3:10])=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:9])=[O:25])=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 14255153Ethyl 2-chloro-5-isocyanatobenzoateHCID 53642952(Z)-3-Amino-2-methyl-2-butenoic Acid Ethyl Ester

Product 1

HCID 54226339Ethyl 2-chloro-5-{3-[2-(ethoxycarbonyl)-1-methylpropenyl]ureido}-benzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.7 g of ethyl 3-amino-2-methylcrotonate, dissolved in 15 ml of absolute diethyl ether, are treated at 23° C., while stirring with a solution of 6.7 g of ethyl 2-chloro-5-isocyanatobenzoate and stirred for 2 hours. The reaction mixture is evaporated to dryness under reduced pressure and the residue is purified by chromatography on 400 g of silica gel using diethyl ether/n-hexane (1:1) as the eluent. There is obtained ethyl 2-chloro-5-{3-[2-(ethoxycarbonyl)-1-methylpropenyl]ureido}-benzoate, m.p. 88°-91° C.

Workup

  1. additionare treated at 23° C.
  2. customThe reaction mixture is evaporated to dryness under reduced pressure
  3. customthe residue is purified by chromatography on 400 g of silica gel

Sources & evidence

ORD record
ord-7cd762ab52a6490ab31df6253daeb11b
Source dataset
uspto-grants-1988_07
Patent number
US04760163

Reaction notes

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