Ethyl chloroacetate → HCID 135665227, compound

HRID 1598390Notes

Reaction equation

HRID 1598390 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[N:12]=[C:11]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[N:10]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38]>CC(=O)CC>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[N:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[N:14]=1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 135804511HCID 135804511, compound

Product 1

HCID 135665227HCID 135665227, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

55.4 g (0.15 mol) of 2-(2,4-dihydroxyphenyl)-4,6-bis-(4-methylphenyl)-1,3,5-triazine are dissolved in refluxing 2-butanone (11) in the presence of 27.6 g (0.2 mol) of K2CO3. A catalytic amount (0.2 g) of KI is added, and 36.8 g (0.3 mol) of ethyl chloroacetate are added dropwise over 1 h30. After refluxing for 25 h, the reaction mixture is cooled in ice, the precipitate is filtered off, washed with water to neutrality and then with methanol. Drying in the oven yields the analytically pure 2-(2-hydroxy-4-ethoxycarbonylmethoxyphenyl)-4,6-bis-(4-methylphenyl)-1,3,5-triazine (54 g, m.p. 166°-167° C.) (Compound No. 47).

Workup

  1. additionA catalytic amount (0.2 g) of KI is added
  2. temperatureAfter refluxing for 25 h
  3. temperaturethe reaction mixture is cooled in ice
  4. filtrationthe precipitate is filtered off
  5. washwashed with water to neutrality
  6. customDrying in the oven

Sources & evidence

ORD record
ord-312e94b79cd3476390c76026606cf460
Source dataset
uspto-grants-1998_04
Patent number
US05736597

Reaction notes

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