Propylene Glycol → Florasulam

HRID 619671Notes

Reaction equation

HRID 619671 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].C(O)C(O)C.Cl[S:16]([C:19]1[N:27]=[C:26]2[N:21]([C:22]([O:29][CH3:30])=[N:23][CH:24]=[C:25]2[F:28])[N:20]=1)(=[O:18])=[O:17]>ClCCl>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH:4][S:16]([C:19]1[N:27]=[C:26]2[N:21]([C:22]([O:29][CH3:30])=[N:23][CH:24]=[C:25]2[F:28])[N:20]=1)(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 1030Propylene GlycolHCID 796472,6-DifluoroanilineHCID 109674702-Chlorosulfonyl-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine

Product 1

HCID 11700495Florasulam

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

A jacketed 250 mL (milliliter) round bottom flask equipped with a stirrer, condenser, and nitrogen inlet and outlet was loaded with 49.1 g (grams), 0.38 mol (mole) of 2,6-difluoroaniline and 25 g of 1,2-propanediol. The mixture was warmed to 35° C. by heating the jacket fluid and a solution of 30.3 g of 93 percent purity (0.10 mol) of 2-chlorosulfonyl-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine in 30.2 g of dichloromethane was added portionwise with stirring under a nitrogen blanket over 3.5 hours. A solid began to form in about one hour and all of the chlorosulfonyl starting material was consumed in 5.5 hours. The resulting mixture was cooled to 20° C. and filtered, collecting the solids. The solids were washed 2×40 mL with methanol and then with 112 g of water. The white solid obtained after drying was found to be the title compound with a purity of greater than 99 percent and to amount to 34.2 g (88.9 percent of theory).

Workup

  1. customA jacketed 250 mL (milliliter) round bottom flask equipped with a stirrer, condenser, and nitrogen inlet and outlet
  2. temperatureby heating the jacket fluid
  3. customto form in about one hour
  4. customall of the chlorosulfonyl starting material was consumed in 5.5 hours
  5. temperatureThe resulting mixture was cooled to 20° C.
  6. filtrationfiltered
  7. customcollecting the solids
  8. washThe solids were washed 2×40 mL with methanol
  9. customThe white solid obtained
  10. customafter drying

Sources & evidence

ORD record
ord-6e55e81db01545bd98c20ea8405072b5
Source dataset
uspto-grants-1999_09
Patent number
US05959106

Reaction notes

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