Glycol monoethyl ether → HCID 23031990, compound

HRID 1674507Notes

Reaction equation

HRID 1674507 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.CC1NC(=O)CC(=O)N=1.C(OCCO)C.[NH2:25][C:26]1[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=1>>[CH3:9][C:4]1[N:5]=[C:6]([Cl:8])[CH:7]=[C:2]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[N:3]=1

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 115683-AminophenolHCID 2349974,6-Dichloro-2-methylpyrimidineHCID 58092440497-30-1

Product 1

HCID 23031990HCID 23031990, compound

Conditions

Temperature
130 °C

Procedure

4,6-dichloro-2-methylpyrimidine (1.63 g, 10.0 mmol) prepared based on the method described in Production Example 2A above using 2-methyl-1H-pyrimidine-4,6-dione instead of the 2-ethyl-1H-pyrimidine-4,6-dione, was slowly added to a 2-ethoxyethanol (5.0 mL) solution of 3-aminophenol (1.09 g, 10.0 mmol) and the reaction mixture heated for 4 hours at 130° C. The reaction was monitored by thin layer chromatography and, following the end of the reaction, the reaction mixture was cooled to room temperature and the precipitated white powder filtered off. The crude product filtered off was used in the subsequent reaction without further purification (1.76 g, crude yield 75%).

Workup

  1. customthe end of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. filtrationthe precipitated white powder filtered off
  4. filtrationThe crude product filtered off
  5. customwas used in the subsequent reaction without further purification (1.76 g, crude yield 75%)

Sources & evidence

ORD record
ord-2ab75054331c4658a52e2b797dc5660a
Source dataset
uspto-grants-2011_08
Patent number
US08003645B2

Reaction notes

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