Ethylamine → 6-Chloro-N-ethyl-5-nitro-2-(trifluoromethyl)pyrimidin-4-amine

HRID 973122Notes

Reaction equation

HRID 973122 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[N:3]=1.[CH2:16]([N:18](CC)CC)[CH3:17].C(N)C>C(O)C>[CH2:16]([NH:18][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[N:3]=1)[CH3:17]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 8471TriethylamineHCID 214008694,6-Dichloro-5-nitro-2-(trifluoromethyl)pyrimidine

Product 1

HCID 214008916-Chloro-N-ethyl-5-nitro-2-(trifluoromethyl)pyrimidin-4-amineYield 97.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.25 g (0.02 mol) of 4,6-dichloro-5-nitro-2-trifluoromethyl-pyrimidine are dissolved in 100 ml of abs. ethanol and the solution is cooled to -30° C. At this temperature, 2.0 g (0.02 mol) of triethylamine and 0.9 g (0.2 mol) of ethylamine are added. The mixture is stirred first for 4 hours at -20° C to -30° C and then for 6 hours at 0° C. After it has been left to stand overnight at 20° C, the reaction mixture is concentrated to dryness. The residue is taken up in ether and the solution washed with water. The ethereal phase is dried and concentrated to yield 5.3 g of 4-ethylamino-6-chloro-5-nitro-2-trifluoromethyl-pyrimidine as a pale yellow oil; nD20 = 1.4985.

Workup

  1. waitfor 6 hours at 0° C
  2. waitAfter it has been left
  3. waitto stand overnight at 20° C
  4. concentrationthe reaction mixture is concentrated to dryness
  5. washthe solution washed with water
  6. customThe ethereal phase is dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4765b102e8364ef38e7e526a682abea1
Source dataset
uspto-grants-1977_10
Patent number
US04055411

Reaction notes

Loading…