1,3-Dibromopropane → 1-(3-bromopropyl)-2,4(1H,3H)-quinazolinedione

HRID 247023Notes

Reaction equation

HRID 247023 reaction equation
C[Si](C)(C)[O:3][C:4]1[N:13]=[C:12]([O:14][Si](C)(C)C)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[Br:21][CH2:22][CH2:23][CH2:24]Br.C(=O)(O)[O-].[Na+]>>[Br:21][CH2:22][CH2:23][CH2:24][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12](=[O:14])[NH:13][C:4]1=[O:3]

Participants

4

Reactant 3

HCID 80011,3-DibromopropaneHCID 516892Sodium BicarbonateHCID 11088105Quinazoline, 2,4-bis[(trimethylsilyl)oxy]-

Product 1

HCID 136872071-(3-bromopropyl)-2,4(1H,3H)-quinazolinedioneYield 25.1%

Procedure

A mixture of 2,4-bis(trimethylsiloxy)-quinazoline (9.14 g) and 1,3-dibromopropane (30 g) was stirred for 2 hours at 130°-140° C. The reaction mixture was cooled at ambient temperature and a mixture of ice-water and saturated sodium bicarbonate aqueous solution was added to the reaction mixture and then the mixture was stirred vigorously to give precipitates. After the mixture was suspended with chloroform, the precipitates were collected by filtration. The precipitates were washed with water and with chloroform respectively and then dried to give 1-(3-bromopropyl)-2,4(1H, 3H)-quinazolinedione (2.12 g) as a crystal, which was used in the next step without purification. m.p. 159°-170° C.

Workup

  1. additionwas added to the reaction mixture
  2. stirringthe mixture was stirred vigorously
  3. customto give
  4. customprecipitates
  5. filtrationthe precipitates were collected by filtration
  6. washThe precipitates were washed with water and with chloroform respectively
  7. customdried

Sources & evidence

ORD record
ord-0d4fd92bdc294498b46628c237570747
Source dataset
uspto-grants-1987_11
Patent number
US04705787

Reaction notes

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