Urea → 6,8-Dichloroquinazoline-2,4(1h,3h)-dione

Reaction equation

[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:13][C:14](N)=[O:15]>>[Cl:12][C:8]1[CH:7]=[C:3]2[C:2](=[C:10]([Cl:11])[CH:9]=1)[NH:1][C:14](=[O:15])[NH:13][C:4]2=[O:5]

Participants

Reactant 2

HCID 1176Urea

HCID 760363,5-Dichloroanthranilic acid

Product 1

HCID 2254696,8-Dichloroquinazoline-2,4(1h,3h)-dione

Procedure

Prepared according to general method C from 2-amino-3,5-dichlorobenzoic acid (3.0 g) and urea (8.8 g). Yield: 3.20 g (95%) of a solid. Although it contained a small amount of an impurity it was used in the next step without further purification. 1H-NMR (DMSO-δ6) δ (ppm) 10.13 (br s, 1H), 7.58 (d, J=2.5 Hz, 1H), 7.50 (d, J=2.6 Hz, 1H).

Workup

customPrepared
customwas used in the next step without further purification

Sources & evidence

ORD record: ord-3c7a744a251344ce9d0e81ac9d894198
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530486B2

Reaction notes

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