Potassium cyanate → 3-Ureidomethyl-phthalic acid dimethyl ester

HRID 448432Notes

Reaction equation

HRID 448432 reaction equation
[O-:1][C:2]#[N:3].[K+].Cl.[CH3:6][O:7][C:8](=[O:21])[C:9]1[C:10](=[C:15]([CH2:19][NH2:20])[CH:16]=[CH:17][CH:18]=1)[C:11]([O:13][CH3:14])=[O:12]>O>[CH3:6][O:7][C:8](=[O:21])[C:9]1[C:10](=[C:15]([CH2:19][NH:20][C:2]([NH2:3])=[O:1])[CH:16]=[CH:17][CH:18]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 21988538Methyl-3-aminomethyl-2-(methoxycarbonyl)benzoate hydrochloride

Product 1

HCID 672293263-Ureidomethyl-phthalic acid dimethyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium cyanate (1.9 g, 22.93 mmol) was added portionwise over 2 hours to a stirred solution of 3-aminomethyl-phthalic acid dimethyl ester hydrochloride (2.0 g, 7.7 mmol) in water (60 mL). After stirred for another 2 hours, the mixture was acidified to pH 4. The mixture was filtered to give 3-ureidomethyl-phthalic acid dimethyl ester (1.4 g, 70%): 1H NMR (DMSO-d6) δ 3.82 (s, 6H), 4.19 d, J=6.0 Hz, 2H), 5.63 (s, 2H), 6.38 (t, J=5.8 Hz, 1H), 7.54-7.62 (m, 2H), 7.78-7.81 (dd, J=2.2 and 6.4 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-09c3678e70f047ce911ed9dc8d4ef467
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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