Bromine → p-Toluenesulfonic acid

HRID 36772Notes

Reaction equation

BrBr.C([O-])(=O)C.[Na+].NC1N=C(N)C=C(O)N=1.O.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24]([OH:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(#N)C.C(O)C.O>[CH3:28][C:18]1[CH:23]=[CH:22][C:21]([S:24]([OH:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To 300 mg (0.766 mmol) of N-4-(1-methoxy-1-buten-4-yl)benzoyl-L-glutamic acid diethyl ester, 3.0 ml of acetonitrile, and 3.0 ml of water, stirred at room temperature, are added 122 mg (0.766 mmol) of bromine in 1 ml of acetonitrile. To this solution is added 188 mg (2.3 mmol) of sodium acetate and 0.97 mg (0.77 mmol) of 2,4-diamino-6-hydroxypyrimidine and the resulting mixture is heated to 60° C. for 18 hours, cooled, then concentrated under vacuum. The resulting residue is triturated (2×5 ml of water) and decanted. Ethanol (5 ml) and 440 mg (2.3 mmol) of p-toluenesulfonic acid monohydrate are added. After heating under reflux for 20 minutes the mixture is cooled to room temperature and filtered. The precipitate is washed with ethanol (2×5 ml) and dried to obtain a p-toluenesulfonate salt of the title compound.

Workup

temperaturecooled
concentrationconcentrated under vacuum
customThe resulting residue is triturated (2×5 ml of water)
customdecanted
temperatureAfter heating
temperatureunder reflux for 20 minutes the mixture
temperatureis cooled to room temperature
filtrationfiltered
washThe precipitate is washed with ethanol (2×5 ml)
customdried

Sources & evidence

ORD record: ord-45b680758579441a831170d55eda758a
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05416211

Reaction notes

Loading…