2,4-Dichloro-5-(2-((trichloromethyl)thio)phenyl)pyrimidine → 2-Chlorobenzo[4,5]thieno[2,3-d]pyrimidine

HRID 711397Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]C(Cl)(Cl)Cl)=[CH:4][N:3]=1>C(N)=O.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[S:15][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2,4-dichloro-5-(2-((trichloromethyl)thio)phenyl)pyrimidine (12.5 g, 33.4 mmol) in formamide (498 ml) was degassed with nitrogen and heated at 60° C. overnight. The reaction solution was cooled to room temperature, diluted with water, filtered and washed with water and a small amount of cold ethanol. White precipitate was recrystallized from EtOH to afford 5.0 g (68% yield) of 2-chlorobenzo[4,5]thieno[2,3-d]pyrimidine as white needles.

Workup

temperatureThe reaction solution was cooled to room temperature
filtrationfiltered
washwashed with water
customWhite precipitate was recrystallized from EtOH

Sources & evidence

ORD record: ord-e3ebb2dfdf4d4be392505a73716cb827
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181270B2

Reaction notes

Loading…