N,N-Diethylaniline → 2-Chloro-5,6,7,8-tetrahydroquinazoline

HRID 2270430Notes

Reaction equation

HRID 2270430 reaction equation
O[C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.CCN(C1C=CC=CC=1)CC.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 1785175505,6,7,8-Tetrahydro-2(1H)-quinazolinone

Product 1

HCID 129338762-Chloro-5,6,7,8-tetrahydroquinazoline

Procedure

A solution of 1 g of 2-hydroxy-5,6,7,8-tetrahydroquinazoline and 0.1 g of diethylaniline in 10 mL of phosphorus oxychloride is refluxed for 2 h, and subsequently cooled and concentrated. The residue is taken up in chloroform and washed with excess 3 N NaOH solution. The organic layer is dried and concentrated to provide 2-chloro-5,6,7,8-tetrahydroquinazoline (1.1 g) as an orange solid.

Workup

  1. temperaturesubsequently cooled
  2. concentrationconcentrated
  3. washwashed with excess 3 N NaOH solution
  4. customThe organic layer is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b2ef82dec904ff88c8e61fd692d4b91
Source dataset
uspto-grants-2001_12
Patent number
US06331629B1

Reaction notes

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