Potassium Carbonate → HCID 9819249, compound

HRID 1352193Notes

Reaction equation

Cl[C:2]1[S:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([Cl:14])[CH:8]=[CH:7][C:5]=2[N:6]=1.[N:15]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[NH:18][CH2:17][CH2:16]2.C(=O)([O-])[O-].[K+].[K+]>C(O)CCCC>[Cl:14][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:18]3[CH:19]4[CH2:22][CH2:23][N:15]([CH2:21][CH2:20]4)[CH2:16][CH2:17]3)[S:3][C:4]=2[C:10]=1[N+:11]([O-:13])=[O:12]

Participants

Conditions

Temperature: 150 °C

Procedure

1.29 g (5.15 mmol) of 2,6-dichloro-7-nitrobenzothiazole, 0.65 g (5.15 mmol) of 1,4-diazabicyclo[3.2.2]nonane, 0.71 g (5.15 mmol) of potassium carbonate and 60 ml of pentan-1-ol are successively introduced into a 250 ml round-bottomed flask. The mixture is heated at 150° C. for 14 h and is then cooled to ambient temperature before being filtered. The solvent is evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel, elution being carried out with a 98/2/0.2 mixture of chloroform, ethanol and aqueous ammonia. After recrystallizing from isopropyl alcohol, 0.54 g of crystals is collected by filtration.

Workup

temperatureis then cooled to ambient temperature
filtrationbefore being filtered
customThe solvent is evaporated under reduced pressure
customthe residue is purified by chromatography on a column of silica gel, elution
additionbeing carried out with a 98/2/0.2 mixture of chloroform, ethanol and aqueous ammonia
customAfter recrystallizing from isopropyl alcohol, 0.54 g of crystals
filtrationis collected by filtration

Sources & evidence

ORD record: ord-e91aed86dfaa4ef29c2a348aaf7c4ea1
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220740B2

Reaction notes

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