Ethylene Glycol → HCID 178521365, compound
Reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].F[C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:18])=[N:13][CH:14]=[N:15]2)=[CH:10][CH:9]=1>CC(N(C)C)=O>[OH:5][CH2:4][CH2:3][O:6][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:18])=[N:13][CH:14]=[N:15]2)=[CH:10][CH:9]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of sodium hydride (60% in oil, 7.67 g, 189.6 mmol) and dimethylacetamide (160 ml) were cooled in an ice-bath under a nitrogen atmosphere and then ethylene glycol (18.2 g, 284 mmol) was slowly added. The reaction mixture was warmed to 60° C. for 10 minutes and then 7-fluoroquinazolin-4-ol (7.75 g, 47.3 mmol) was slowly added. The reaction mixture was heated to 110° C. for 16 hours and then the mixture was concentrated to approximately half volume. The mixture was poured into water and the pH of the solution was adjusted to 5 with dilute hydrochloric acid. The resultant precipitate was filtered and then dried in a vacuum oven at 65° C. for 16 hours. The residue was triturated with diethyl ether to give 7-(2-hydroxyethoxy)quinazolin-4-ol (4.4 g) as an off white solid which was used in subsequent steps without further purification: MS (+ve ESI): 207 (M+H)+ MS (−ve ESI): 205 (M−H)−.
Workup
- temperaturewere cooled in an ice-bath under a nitrogen atmosphere
- temperatureThe reaction mixture was heated to 110° C. for 16 hours
- concentrationthe mixture was concentrated to approximately half volume
- additionThe mixture was poured into water
- filtrationThe resultant precipitate was filtered
- customdried in a vacuum oven at 65° C. for 16 hours
- customThe residue was triturated with diethyl ether
Sources & evidence
- ORD record
- ord-d4801c6e31874bc0a52a29d108139116
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691867B2
Reaction notes
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