Ammonia → 6-Chloroquinazoline-2,4(1H,3H)-diimine

HRID 1187254Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].Cl.Cl[C:13](N)=[NH:14].S1(CCCC1)(=O)=O.CS(C)(=O)=O.[NH3:28]>O>[Cl:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[N:1]=[C:13]([NH2:14])[N:5]=[C:4]2[NH2:28]

Participants

Conditions

Temperature: 165 °C

Procedure

A mixture of 2-amino-5-chlorobenzonitrile (1.07 g, 7.0 mmol), chloro-formamidine hydrochloride (1.6 g, 14 mmol), sulfolane (0.5 ml) and dimethylsulfone (3 g) was heated at 165° C. for 30 minutes. Then, water (30 ml) was added to the reaction mixture. The pH was adjusted to 7-8 by the addition of a 33% aqueous ammonia solution in water. The precipitate was collected by filtration, washed with water and dried over P2O5, yielding the title compound as a yellowish solid (1.35 g, yield: 99%) which was characterized by its mass spectrum as follows: MS (m/z): 195 ([M+H]+, 100).

Workup

filtrationThe precipitate was collected by filtration
washwashed with water
dry with materialdried over P2O5

Sources & evidence

ORD record: ord-e5e385ea914a486da22f9be0f2531dd1
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673929B2

Reaction notes

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