2,4-Dichlorophenyl isocyanate → 3-(2,4-Dichlorophenyl)-6-fluoroquinazoline-2,4(1H,3H)-dione

HRID 1735969Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[O:11].[F:12][C:13]1[CH:23]=[C:17]([C:18](OCC)=[O:19])[C:16]([NH2:24])=[CH:15][CH:14]=1.C[O-].[Na+]>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18](=[O:19])[C:17]2[C:16](=[CH:15][CH:14]=[C:13]([F:12])[CH:23]=2)[NH:24][C:10]1=[O:11]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 2,4-dichlorophenyl isocyanate (18.8 g, 0.10 mol) in N-methylpyrrolidone (50 ml) is metered at room temperature into a solution of ethyl 5-fluoroanthranilate (18.3 g, 0.10 mol) in N-methylpyrrolidone (70 ml). After addition is complete, the mixture is stirred at 90° C. for 2 hours. 1.80 ml of a 30% strength solution of methanolic sodium methoxide (0.010 mol) are metered in and the mixture is stirred under reflux for a further 2 hours, ethanol and methanol being distilled off. After cooling, the product is precipitated by addition of dilute hydrochloric acid (100 ml). The product is then filtered off with suction, washed with water and dried. 29.8 g of 3-(2,4-dichlorophenyl)-6-fluoro-2,4(1H,3H)-quinazolinedione (yield: 91.7% of theory) of melting point 311° to 313° C. are obtained.

Workup

additionAfter addition
stirringis stirred
temperatureunder reflux for a further 2 hours
distillationethanol and methanol being distilled off
temperatureAfter cooling
customthe product is precipitated by addition of dilute hydrochloric acid (100 ml)
filtrationThe product is then filtered off with suction
washwashed with water
customdried

Sources & evidence

ORD record: ord-5ccbc9feb3244fffa980c2b49e62b9cc
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05539114

Reaction notes

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