N-bromobutanimide → HCID 136354606, compound

HRID 1287500Notes

Reaction equation

HRID 1287500 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]([C:12]1[NH:21][C:20](=[O:22])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[N:13]=1)=[CH:10][CH3:11]>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:11][CH:10]=[CH:9][C:12]1[NH:21][C:20](=[O:22])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[N:13]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 136354607HCID 136354607, compound

Product 1

HCID 136354606HCID 136354606, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

16.0 g (0.08 moles) of N-bromosuccinimide, 14.0 g (0.07 moles) of 2-propenyl-6-methyl-4(3H)-quinazolone and 0.05 g of dibenzoylperoxide in 500 mls. of carbon tetrachloride are boiled under a reflux for 16 hours. The reaction mixture is evaporated to dryness in vacuo and the succinimide is remoed from the residue by boiling out with water several times. The residue which has been purified in this way is then purified by dissolving once again in a 9:1 mixture of methyl alcohol/chloroform and in this way one obtains 8.5 g (38% of theory) of 2-(3-bromopropenyl)-6-methyl-4(3H)-quinazolone with a melting point of 197°-198° C. c. 4.0 g (0.0144 moles) of 2-(3-bromopropenyl)-6-methyl-4(3H)-quinazolone are heated for 5 hours to 80° C with 5.4 g (0.0288 moles) of 1-(2-methoxyphenyl) piperazine in 50 mls. of dimethylformamide. The reaction mixture is then distributed between 10% aqueous ammonia and chloroform and the chloroform phase is evaporated to dryness after drying over calcined potassium carbonate. The residue is purified by crystallisation twice from ethyl acetate. In this way one obtains 5.4 g (96.5% of theory) of 2-(3-(1-(2-methoxyphenyl) piperazinyl-4) prop-2-en-1-yl)-6-methyl-4(3H)-quinazolone with a melting point of 169°-170° C. Using the same mode of operation, when choosing suitable initial materials, one obtains the piperazinylalkyl-4-(3H)-quinazolones described in Examples 1 to 24.

Workup

  1. temperaturea reflux for 16 hours
  2. customThe reaction mixture is evaporated to dryness in vacuo
  3. customThe residue which has been purified in this way
  4. customis then purified
  5. dissolutionby dissolving once again in a 9:1 mixture of methyl alcohol/chloroform and in this way one

Sources & evidence

ORD record
ord-730a19d25a93450f841382faa824c939
Source dataset
uspto-grants-1976_10
Patent number
US03984555

Reaction notes

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