Phosphorus oxychloride → 4-Chloro-7,8-dihydro[1,4]dioxino[2,3-g]quinazoline

HRID 1917671Notes

Reaction equation

HRID 1917671 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]3[O:14][CH2:13][CH2:12][O:11][C:8]=3[CH:9]=2)[C:4](=O)[NH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:18]>C1(C)C=CC=CC=1>[Cl:18][C:4]1[C:5]2[C:10](=[CH:9][C:8]3[O:11][CH2:12][CH2:13][O:14][C:7]=3[CH:6]=2)[N:1]=[CH:2][N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1357365997,8-dihydro-[1,4]dioxino[2,3-g]quinazolin-4(3H)-one

Product 1

HCID 189328674-Chloro-7,8-dihydro[1,4]dioxino[2,3-g]quinazolineYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

According to the procedure described in Example 6A Step 5, a mixture of 7,8-dihydro-[1,4]dioxino[2,3-g]quinazolin-4(3H)-one (1.114 g, 5.46 mmol) and POCl3 (10 mL) in toluene (10 mL) was heated at 125° C. for 5 hours to afford 4-chloro-7,8-dihydro-[1,4]dioxino[2,3-g]quinazoline as a solid (1.143 g, 94%). 1H NMR (300 MHz, CDCl3) δ 8.90 (s, 1H), 7.70 (s, 1H), 7.65 (s, 1H), 4.46 (m, 4H).

Sources & evidence

ORD record
ord-6a6f65869b9044d0944fe2f3695e36c8
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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