Ammonia → Aminocyclopyrachlor

HRID 218303Notes

Reaction equation

HRID 218303 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].Cl>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

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 582208065,6-Dichloro-2-cyclopropylpyrimidine-4-carboxylic acid

Product 1

HCID 17747875AminocyclopyrachlorYield 105.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A 3-L flask was charged with 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (280 g, 1.2 mol), ammonia (28 wt % in water, 350 g, 5.76 mol) and water (1.26 L). The reaction mixture was heated at 80° C. for 5 h, and excess water (about 600 mL) was removed by distillation at 50° C./9 kPa. After cooling to 20° C., the reaction mixture was acidified to pH 2 with aqueous hydrochloric acid (132 g, 110 mL, 1.32 mol), cooled to 5° C., and filtered. The filtered wet cake was washed with water (2×200 mL) and dried in a vacuum-oven at 55° C. to give about 270 g of the title compound as a monohydrate, which contained 8.3 wt % of water measured by Karl Fischer titration, and decomposed at 152° C. (after crystallization from hot ethanol).

Workup

  1. customexcess water (about 600 mL) was removed by distillation at 50° C./9 kPa
  2. temperatureAfter cooling to 20° C.
  3. temperaturecooled to 5° C.
  4. filtrationfiltered
  5. washThe filtered wet cake was washed with water (2×200 mL)
  6. customdried in a vacuum-oven at 55° C.

Sources & evidence

ORD record
ord-1e893584edd54dbe8b68d35a1987f58b
Source dataset
uspto-grants-2012_06
Patent number
US08198442B2

Reaction notes

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