Ammonia → Aminocyclopyrachlor

HRID 249657Notes

Reaction equation

HRID 249657 reaction equation
[Cl:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[N:4][C:5]([CH:9]2[CH2:11][CH2:10]2)=[N:6][C:7]=1Cl.[NH3:15]>O>[NH2:15][C:7]1[N:6]=[C:5]([CH:9]2[CH2:11][CH2:10]2)[N:4]=[C:3]([C:12]([OH:14])=[O:13])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 582208065,6-Dichloro-2-cyclopropylpyrimidine-4-carboxylic acid2×

Product 1

HCID 17747875Aminocyclopyrachlor

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (i.e. the product of Step C1 or C2) (5.1 g, 22 mmol), water (30 mL) and aqueous ammonia (28%, 8 g, 130 mmol) was heated at 80° C. for 3 h. The solution was concentrated at 50° C. and 70 torr (9.3 kPa) pressure to about half volume to remove most of the excess ammonia. The resulting slurry was stirred at 20° C., acidified to pH 2 with aqueous hydrochloric acid, cooled to 5° C. and filtered. The isolated solid was dried in a vacuum oven to afford the title product (4.2 g), a compound of the present invention.

Workup

  1. concentrationThe solution was concentrated at 50° C.
  2. custom70 torr (9.3 kPa) pressure to about half volume to remove most of the excess ammonia
  3. temperaturecooled to 5° C.
  4. filtrationfiltered
  5. customThe isolated solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-ff1c3bf9e38e4142b276aba472c36225
Source dataset
uspto-grants-2011_01
Patent number
US07863220B2

Reaction notes

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