Sulfuryl chloride → Ethoxysulfuron

HRID 2380011Notes

Reaction equation

HRID 2380011 reaction equation
[O-:1][C:2]#[N:3].[Na+].[S:5](Cl)(Cl)(=[O:7])=[O:6].[CH2:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[CH3:11].[NH2:20][C:21]1[N:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[N:22]=1>C(#N)C>[CH2:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][S:5]([NH:3][C:2]([NH:20][C:21]1[N:22]=[C:23]([O:29][CH3:30])[CH:24]=[C:25]([O:27][CH3:28])[N:26]=1)=[O:1])(=[O:7])=[O:6])[CH3:11]

Participants

6

Reactant 4

HCID 24648Sulfuryl chlorideHCID 667552-EthoxyphenolHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 517096Sodium Cyanate

Product 1

HCID 3623881Ethoxysulfuron

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

26.0 g (0.4 mol) of comminuted sodium cyanate are suspended at room temperature in 200 ml of acetonitrile, and 28.3 g (0.21 mol) of sulfuryl chloride are added within the space of 20 min, during which time the temperature rises to 44° C. After stirring for a further four hours at 50° C., the mixture is distilled under reduced pressure, cooled to 27° C. and 27.6 g (0.2 mol) of 2-ethoxyphenol are added within the space of 10 min. The mixture is left to stand overnight and 15.5 g (0.1 mol) of 2-amino-4,6-dimethoxypyrimidine are added at room temperature. The mixture is stirred at 50° C. for a further 120 min, the solvent is removed under reduced pressure, 100 ml of water are added, and the mixture is extracted with dichloromethane. After distilling off the organic solvent, 49.9 g of solids remain which, according to HPLC, exhibit a content of 71.6% by weight of 1-(2-ethoxyphenoxysulfonyl)-3-(4,6-dimethoxy-2-pyrimidyl)-urea. The yield of the compound is about 89% of theory.

Workup

  1. customrises to 44° C
  2. distillationthe mixture is distilled under reduced pressure
  3. temperaturecooled to 27° C.
  4. waitThe mixture is left
  5. waitto stand overnight
  6. stirringThe mixture is stirred at 50° C. for a further 120 min
  7. customthe solvent is removed under reduced pressure, 100 ml of water
  8. additionare added
  9. extractionthe mixture is extracted with dichloromethane
  10. distillationAfter distilling off the organic solvent, 49.9 g of solids

Sources & evidence

ORD record
ord-6554c43988024234bb9e96b010f51c36
Source dataset
uspto-grants-1994_11
Patent number
US05364937

Reaction notes

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