Water → HCID 135838396, compound

HRID 2308694Notes

Reaction equation

HRID 2308694 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]1[NH:12][C:13](=[O:15])[CH2:14][N:6]1[CH2:5]2.Br[CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:15]=[C:13]1[CH2:14][N:6]2[C:7](=[N:8][C:9]3[C:4]([CH2:5]2)=[CH:3][C:2]([O:1][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][CH:10]=3)[NH:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 135838394HCID 135838394, compound

Product 1

HCID 135838396HCID 135838396, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7-hydroxy-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-2-one (2.6 g) made as per U.S. Pat. No. 3,932,407 and ethyl 4-bromobutyrate (1.72 ml) in 100 ml dimethylformamide was added 1.86 g potassium carbonate. The reaction mixture was sealed under a blanket of nitrogen and heated to 100° C. for 4 hours. The reaction mixture was cooled, poured into 100 ml of water, and the resulting precipitate collected by filtration. Recrystallization from dimethylformamide-water gave ethyl 4-(2-oxo-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxybutyrate, m.p. 243°-244° C.

Workup

  1. customThe reaction mixture was sealed under a blanket of nitrogen
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe resulting precipitate collected by filtration
  4. customRecrystallization from dimethylformamide-water

Sources & evidence

ORD record
ord-dad4ae2d498a4ae198cde0504be4c685
Source dataset
uspto-grants-1987_09
Patent number
US04690925

Reaction notes

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