Acetic Acid → HCID 135823916, compound

HRID 1579989Notes

Reaction equation

HRID 1579989 reaction equation
[NH:1]1[C:5]2=[N:6][C:7]3[C:12]([CH2:13][N:4]2[CH2:3][C:2]1=[O:14])=[CH:11][CH:10]=[CH:9][CH:8]=3.C(O)(=O)C.[Br:19]Br>O>[Br:19][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[C:5]1[NH:1][C:2](=[O:14])[CH2:3][N:4]1[CH2:13]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 135485711Imidazo[2,1-b]quinazolin-2(3H)-one, 1,5-dihydro-

Product 1

HCID 135823916HCID 135823916, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a vigorously stirred solution of 1.87 g. (0.01 mole) of 1,2,3,5-tetrahydroimidazo[2,1-b]-quinazolin-2-one in 40 ml. of glacial acetic acid was added dropwise at room temperature 1.60 g. (0.01 mole) of bromine. The mixture was stirred at room temperature for one hour, water (50 ml.) was added and the volume concentrated (10-15 ml.) in vacuo. Additional water (50 ml.) was added, the solution made basic with ammonium hydroxide, warmed and the insoluble material filtered under suction. The colorless solid was washed with water, dried and crystallized from 50 ml. of 5% hydrochloric acid yielding 0.8 g. (30% yield) of a colorless solid: m.p. >275°. Purification was effected by crystallization from methanol/ether; m.p. 275° to yield the title product.

Workup

  1. concentrationthe volume concentrated (10-15 ml.) in vacuo
  2. additionAdditional water (50 ml.) was added
  3. temperaturewarmed
  4. filtrationthe insoluble material filtered under suction
  5. washThe colorless solid was washed with water
  6. customdried
  7. customcrystallized from 50 ml

Sources & evidence

ORD record
ord-e0a1447108fb41e1bbbb3a67d3f4f3be
Source dataset
uspto-grants-1976_01
Patent number
US03932407

Reaction notes

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