Methanol → Cyclosulfamuron

HRID 744890Notes

Reaction equation

HRID 744890 reaction equation
[CH3:1][O-:2].[Na+].[CH:4]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][S:16]([NH:19][C:20]([NH:22][C:23]2[N:28]=[C:27](Cl)[CH:26]=[C:25](Cl)[N:24]=2)=[O:21])(=[O:18])=[O:17])=[O:8])[CH2:6][CH2:5]1.[CH3:31][OH:32]>>[CH:4]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][S:16]([NH:19][C:20]([NH:22][C:23]2[N:28]=[C:27]([O:2][CH3:1])[CH:26]=[C:25]([O:32][CH3:31])[N:24]=2)=[O:21])(=[O:18])=[O:17])=[O:8])[CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 887Methanol3×HCID 10942334Sodium Methoxide2×HCID 110263731-{[o-(Cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dichloro-2-pyrimidinyl)urea

Product 1

HCID 6451137CyclosulfamuronYield 70%

Conditions

Temperature
60 °C

Procedure

A mixture of sodium methoxide (1.08 g, 0.02 mol) in methanol is added slowly to a mixture of 1-{[o-(cyclopropyl)phenyl]sulfamoyl}-3-(4,6-dichloro-2-pyrimidinyl)urea from Example 1 (4.30 g, 0.01 mol) in methanol at 60° C. The reaction mixture is heated at 60° C. for two hours, cooled, treated with additional sodium methoxide (0.54 g), refluxed overnight, cooled, acidified and concentrated in vacuo to obtain a residue. The residue is slurried in methanol, filtered, washed sequentially with methanol and water, and dried in a vacuum oven at 55°-60° C. to give the title product as a cream colored solid (2.2 g, 98.6% real by HPLC analysis, 70% yield, mp 168.5°-169.5° C.).

Workup

  1. temperaturecooled
  2. temperaturerefluxed overnight
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue
  6. filtrationfiltered
  7. washwashed sequentially with methanol and water
  8. customdried in a vacuum oven at 55°-60° C.

Sources & evidence

ORD record
ord-327c11575e17438b8e1ae817c0f73648
Source dataset
uspto-grants-1996_09
Patent number
US05559234

Reaction notes

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