Methanol → Aminocyclopyrachlor-methyl

HRID 2403100Notes

Reaction equation

HRID 2403100 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]([OH:13])=[O:12])[C:3]=1[Cl:14].S(Cl)(Cl)=O.[CH3:19]O>>[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]([O:13][CH3:19])=[O:12])[C:3]=1[Cl:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 17747875Aminocyclopyrachlor2×

Product 1

HCID 16725794Aminocyclopyrachlor-methyl

Conditions

Temperature
60 °C

Procedure

To a solution of 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (i.e. the product of Step D1 or D2 of Example 2) (8.5 g, 40 mmol) in methanol (120 mL) was added dropwise with cooling thionyl chloride (15 mL, 200 mmol). The mixture was heated at 60° C. for 24 h. The mixture was concentrated to 25% of the original volume and diluted with water (100 mL). Phenolphthalein pH indicator was added, and 10% aqueous sodium hydroxide was added dropwise with cooling at 10-20° C. to bring the pH to 8-10. The solid was isolated by filtration, washed with water and dried in a vacuum oven at 50-60° C. to afford the title product (7.3 g), a compound of the present invention.

Workup

  1. concentrationThe mixture was concentrated to 25% of the original volume
  2. additiondiluted with water (100 mL)
  3. additionPhenolphthalein pH indicator was added
  4. addition10% aqueous sodium hydroxide was added dropwise
  5. temperaturewith cooling at 10-20° C.
  6. customThe solid was isolated by filtration
  7. washwashed with water
  8. customdried in a vacuum oven at 50-60° C.

Sources & evidence

ORD record
ord-599b817baf804bd5af94891e8aa8308a
Source dataset
uspto-grants-2014_08
Patent number
US08802597B2

Reaction notes

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