2-Chloroaniline → HCID 21284435, compound

HRID 2232125Notes

Reaction equation

[OH:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][OH:14])[N:8]=[C:7](Cl)[N:6]=1.[Cl:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19].[OH-].[Na+]>O>[OH:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][OH:14])[N:8]=[C:7]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[Cl:16])[N:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

6.8 g (0.053 mol) of 2,4-bis-(2-hydroxyethylamino)-6-chloro-1,3,5-triazine, 11.7 g (0.05 mol) of 2-chloroaniline and 85 ml of water are placed in a 250 ml flask equipped with a stirrer, a dropping funnel, a reflux condenser and a thermometer. The mixture is heated with stirring to 90° C., in the course of which a clear solution is formed. A solution of 2 g of sodium hydroxide in 15 ml of water is added dropwise to this mixture, and the whole mixture is heated under reflux for 3 hours. After cooling, the aqueous system is in 2 phases. The supernatant inorganic phase is discarded. The lower phase is extracted by boiling with toluene, the product being obtained in the residue. The melting point is 108°-110° C. and, after reprecipitation with ethyl acetate/petroleum ether, is 112°-114° C. The yield is 82% of theory.

Workup

customequipped with a stirrer, a dropping funnel, a reflux condenser
temperatureThe mixture is heated
customis formed
temperaturethe whole mixture is heated
temperatureunder reflux for 3 hours
temperatureAfter cooling
extractionThe lower phase is extracted
customthe product being obtained in the residue
customThe melting point is 108°-110° C. and, after reprecipitation with ethyl acetate/petroleum ether
customis 112°-114° C

Sources & evidence

ORD record: ord-5947753365774ebe89e7193faf73f0fb
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04786672

Reaction notes

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