3-Chloroaniline → (3-Chlorophenyl)-(4-chloro-[1,3,5]triazin-2-yl)amine

HRID 1815920Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>C(C#N)(C)=O>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=2)[CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2,4-dichloro-1,3,5-triazine (4.0 g, 26.7 mmol) and solid K2CO3 (16.0 g, 116 mmol) was suspended in AcCN (50 mL) under nitrogen at 0° C. followed by addition of 3-chloroaniline (3.4 g, 26.7 mmol). The mixture was stirred at 0° C. for 0.5 h. The reaction was quenched by pouring onto ice/water. The white solid which formed was collected by suction filtration, dried under vacuum then purified by column chromatography (elution with CH2Cl2) to give (3-chlorophenyl)-(4-chloro-[1,3,5]triazin-2-yl)amine MS m/z=241. Calc'd for C9H6Cl2N4: 240.00.

Workup

customThe reaction was quenched
additionby pouring onto ice/water
customThe white solid which formed
filtrationwas collected by suction filtration
customdried under vacuum
customthen purified by column chromatography (elution with CH2Cl2)

Sources & evidence

ORD record: ord-6c7f2c9f51374ba9b8c32cf0065e5a3a
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881737B2

Reaction notes

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