Chlorosulfonic acid → Ametoctradin

HRID 1887185Notes

Reaction equation

HRID 1887185 reaction equation
ClS(O)(=O)=O.[NH2:6][C:7]1[N:11]=[CH:10][NH:9][N:8]=1.[C:12]([CH:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:17]#[N:18])(=O)[CH2:13][CH3:14]>O.CC1C=CC=CC=1C>[CH2:13]([C:12]1[C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:17]([NH2:18])[N:8]2[N:9]=[CH:10][N:11]=[C:7]2[N:6]=1)[CH3:14]

Participants

6

Reactant 3

HCID 24638Chlorosulfonic acidHCID 534342362-(1-Oxopropyl)decanenitrileHCID 178418311HCID 178418311, compound

Product 1

HCID 15604010AmetoctradinYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

In a 2.5 l jacketed vessel fitted with condenser and water separator, 737 g of o-xylene was initially charged, and 39.5 g of chlorosulfonic acid was added. 191.2 g of 3-amino-1,2,4-triazole and 1254 g of a solution of 2-propionyldecanonitrile (37.7% by weight in o-xylene) were added, and the mixture was heated to reflux. The mixture was stirred under reflux for 12 hours, and the water of reaction formed was removed via a phase separator. Once no more water was separated off, the mixture was cooled to 140° C. and 59.4 g of triethylamine were added. On further cooling, the product precipitated in the form of colorless crystals. At a temperature 105° C., 152.8 g of methanol were added. The mixture was cooled further to 20° C., and the solid formed was separated off. The filtercake was washed with a mixture of 850 g of methanol and 119 g of water and then dried under reduced pressure. This gave 525.5 g of colorless crystals having a content of 98.3% a/a (HPLC). The title compound was obtained as a mixture of two modifications having melting points of 199° C. and 201° C., respectively. Yield: 83.0%.

Workup

  1. customfitted with condenser
  2. temperaturethe mixture was heated to reflux
  3. temperatureunder reflux for 12 hours
  4. customformed
  5. customwas removed via a phase separator
  6. customOnce no more water was separated off
  7. addition59.4 g of triethylamine were added
  8. customOn further cooling, the product precipitated in the form of colorless crystals
  9. additionAt a temperature 105° C., 152.8 g of methanol were added
  10. temperatureThe mixture was cooled further to 20° C.
  11. customthe solid formed
  12. customwas separated off
  13. washThe filtercake was washed with a mixture of 850 g of methanol and 119 g of water
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-55a140b649bd40c987363d28e3d5db4c
Source dataset
uspto-grants-2013_08
Patent number
US08501748B2

Reaction notes

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