Methyl iodide → 1-Isopropyl-2-methylsulfanyl-1H-imidazole-4,5-dione

Isopropyl thiourea 9 (8.0 g, 67.7 mmol) in 100 ml of dry acetone was added iodomethane (6.3 ml, 101 mmol) dropwise at room temperature. After the addition was completed, the mixture was refluxed for 1 hour, and the solvent was evaporated to dryness under the reduced pressure to give a gum. The gummy hydroiodide salt was suspended in 200 ml of dry methylene chloride and to the suspension was added triethylamine (37.7 ml, 270 mmol). The mixture was stirred for 30 minutes at room temperature, cooled down to −78° C. with a dry ice/acetone bath. To the mixture was added dropwise oxalyl chloride (40.6 ml of 2M solution, 81.2 mmol) and stirred at −78° C. for 1 hour. The reaction was quenched by addition of water to decompose the excess oxalyl chloride, the solvent was dried over Na2SO4 and evaporated to dryness in vacuo.

1. additionAfter the addition
2. temperaturethe mixture was refluxed for 1 hour
3. customthe solvent was evaporated to dryness under the reduced pressure
4. customto give a gum
5. temperaturecooled down to −78° C. with a dry ice/acetone bath
6. stirringstirred at −78° C. for 1 hour
7. customThe reaction was quenched by addition of water
8. dry with materialthe solvent was dried over Na2SO4
9. customevaporated to dryness in vacuo

ORD record

ord-7225e4e670a849dc983aa77980caefcf

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07101902B2