1,3-Dichloro-5,5-dimethylhydantoin → 2-(3-Dodecoxypropylcarbamoyl)-4-chloro-5-isobutoxycarbonylamino-1-naphthol

HRID 1379807

Reaction equation

HRID 1379807 reaction equation
[CH2:1]([O:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[NH:30][C:31]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:32])[C:21]=1[OH:38])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Cl:39]N1C(C)(C)C(=O)N(Cl)C1=O.C(OCC)(=O)C>CC(C)=O>[CH2:1]([O:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([C:20]1[CH:29]=[C:28]([Cl:39])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[NH:30][C:31]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:32])[C:21]=1[OH:38])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 8857Ethyl AcetateHCID 117631581-hydroxy-5-(2-methylpropyloxycarbonylamino)-N-(3-dodecyloxypropyl)-2-naphthoamide

Product 1

HCID 108970372-(3-Dodecoxypropylcarbamoyl)-4-chloro-5-isobutoxycarbonylamino-1-naphtholYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 30 ml of acetone, 5.28 g (0.01 mol) of 2-(3-dodecoxypropylcarbamoyl)-5-isobutoxycarbonylamino-1-naphthol synthesized in accordance with the method described in JP-A No. 123158/1987 was dissolved and 2.00 g (0.01 mol) of 1,3-dichloro-5,5-dimethylhydantoin was added to the solution, followed by stirring for 2 hours at room temperature. Then 50 ml of ethyl acetate was added to the reaction mixture, followed by washing with a 5% aqueous sodium hydroxide solution and then washing with water. The solvent was distilled off and crystallization from acetonitrile was carried out, to give 5.17 g (yield: 92%) of 2-(3-dodecoxypropylcarbamoyl)-4-chloro-5-isobutoxycarbonylamino-1-naphthol

Workup

  1. dissolution123158/1987 was dissolved
  2. washby washing with a 5% aqueous sodium hydroxide solution
  3. washwashing with water
  4. distillationThe solvent was distilled off
  5. customcrystallization from acetonitrile

Sources & evidence

ORD record
ord-01338e7427954cba8caf3efa424dfcb0
Source dataset
uspto-grants-1997_09
Patent number
US05672714

Linked notes

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