N,N-Dimethylaniline → HCID 10263274, compound

HRID 1973879Notes

Reaction equation

HRID 1973879 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:15][C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.P(Cl)(Cl)([Cl:19])=O.CN(C)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O.C(Cl)(Cl)Cl>[Cl:19][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[N:15]=1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 135473199HCID 135473199, compound

Product 1

HCID 10263274HCID 10263274, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

A 2.12 g portion of 2-(2-furyl)quinazolin-4(3H)-one was stirred into 25 ml of phosphorus oxychloride and to this mixture was slowly added 1.21 g of dimethylaniline. This mixture was stirred for 15 minutes. The entire mixture was added slowly to 1 liter of cold water containing 25 ml of chloroform. Solid sodium bicarbonate was added as required to keep the water solution basic. The chloroform extract was separated and the water extracted with an additional 25 ml of chloroform. The chloroform extracts were combined and concentrated to give a yellow solid. The solid was recrystallized from cyclohexane to give 1.4 g of 4-chloro-2-(2-furyl)quinazoline, m.p. 116°-118°; ir and nmr spectra were consistent with the assigned structure.

Workup

  1. extractionThe chloroform extract
  2. customwas separated
  3. extractionthe water extracted with an additional 25 ml of chloroform
  4. concentrationconcentrated
  5. customto give a yellow solid
  6. customThe solid was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-0674251f3d2c4c689f578a7b75a396f8
Source dataset
uspto-grants-1976_12
Patent number
US03998951

Reaction notes

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