Ethanol → HCID 178517509, compound

HRID 1010854Notes

Reaction equation

HRID 1010854 reaction equation
CO[C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10])=O.[F:11][C:12]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:13]=1[C:14]([NH2:16])=[NH:15].[CH2:22](O)C>>[Cl:21][C:18]1[CH:19]=[CH:20][C:12]([F:11])=[C:13]([C:14]2[N:16]=[C:6]([OH:10])[C:5]3[CH2:3][CH2:22][CH2:7][CH2:8][C:9]=3[N:15]=2)[CH:17]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 219309795-Chloro-2-fluorobenzene-1-carboximidamide

Product 1

HCID 178517509HCID 178517509, compoundYield 78%

Conditions

Temperature
80 °C

Procedure

To a solution of methyl-2-oxocyclopentane carboxylate (2 g, 11.8 mmol, 1 eq), in dry ethanol (20 ml) was added a solution of 2-fluoro-5-chlorobenzamidine (2.04 g, 11.8 mmol, 1 eq) in ethanol (20 ml) and the reaction mixture was heated to 80° C. overnight. The reaction mixture was cooled to r.t. and the solvent was removed in vacuo to afford a crude residue which was purified by recrystallization from hot ethyl acetate to afford 2-(5-chloro-2-fluorophenyl)-5,6,7,8-tetrahydroquinazolin-4-ol (2.56 g, 78%) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to r.t.
  2. customthe solvent was removed in vacuo
  3. customto afford a crude residue which
  4. customwas purified by recrystallization from hot ethyl acetate

Sources & evidence

ORD record
ord-d17f51ae829847169f4dc54ed83f8a55
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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