Triethylamine → ethyl N-(2,4-dichlorophenylcarbamoyl)-5-fluoroanthranilate

HRID 1735971Notes

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]([O:20][CH2:21][CH3:22])=[O:19])[C:16]([NH2:24])=[CH:15][CH:14]=1.C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:24][C:16]1[C:17](=[CH:23][C:13]([F:12])=[CH:14][CH:15]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:11]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 2,4-dichlorophenyl isocyanate (47.0 g, 0.25 mol) in xylene (130 ml) is metered at room temperature into a solution of ethyl 5-fluoroanthranilate (45.2 g, 0.25 mol) in xylene (210 ml). After addition is complete, the mixture is stirred at 90° C. for 2 hours. Triethylamine (3.5 ml, 2.55 g, 0.025 mol) is metered in. The mixture is stirred at 90° C. for a further 2 hours. After cooling, the product is filtered off with suction and washed with 3×30 ml of xylene and dried. 86.9 g of ethyl N-(2,4-dichlorophenylcarbamoyl)-5-fluoroanthranilate of melting point 219° to 223° C. (decomposition) are obtained. The cyclization product 3-(2,4-dichlorophenyl)-6-fluoro-2,4(1H,3H)-quinazolinedione cannot be detected by thin-layer chromatography.

Workup

additionAfter addition
stirringThe mixture is stirred at 90° C. for a further 2 hours
temperatureAfter cooling
filtrationthe product is filtered off with suction
washwashed with 3×30 ml of xylene
customdried

Sources & evidence

ORD record: ord-72acfa54c5334fcca626f2a0f7f1f62d
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05539114

Reaction notes

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