Benzaldehyde → HCID 20499629, compound

HRID 1395259Notes

Reaction equation

HRID 1395259 reaction equation
[CH:1]1([CH2:4][N:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:6]([NH2:8])=[S:7])[CH2:3][CH2:2]1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Br.O>C1(C)C=CC=CC=1>[CH:1]1([CH2:4][N:5]2[C:9]3[C:10](=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)[CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:8][C:6]2=[S:7])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 260Hydrogen BromideHCID 962WaterHCID 54541178HCID 54541178, compound

Product 1

HCID 20499629HCID 20499629, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2.36 g (0.01 mole) of N-cyclopropylmethyl-N-(p-methoxyphenyl) thiourea in 30 ml of toluene were added 1.21 g (0.011 mole) of benzaldehyde and 0.84 g (0.005 mole) of 48% hydrobromic acid. The resulting mixture was heated under reflux for 6 hours using a water separator. After cooling, the reaction mixture was washed with dilute hydrochloric acid and then with water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was recrystallized from isopropyl alcohol to give 2.33 g (72%) of 1-cyclopropylmethyl-4-phenyl-6-methoxy-3,4-dihydro-2(1H)-quinazolinethione, m.p. 146°-147° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with dilute hydrochloric acid
  5. dry with materialwith water, and dried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-44be8938f6894447986681353f4580bf
Source dataset
uspto-grants-1980_05
Patent number
US04202974

Reaction notes

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