Hydrochloric Acid → HCID 57651846, compound

HRID 907411Notes

Reaction equation

HRID 907411 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[H-].[Na+].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1.Cl>C1COCC1.CCOCC.C(OCC)(=O)C>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:1][C:21](=[O:22])[NH:20][C:17]2[CH:18]=[CH:19][C:14]([C:13]([F:12])([F:24])[F:23])=[CH:15][CH:16]=2)[N:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 655222-Amino-4,6-dichloropyrimidineHCID 737684-(Trifluoromethyl)phenyl isocyanate

Product 1

HCID 57651846HCID 57651846, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-4,6-dichloropyrimidine (4.10 g, 25 mmol) in anhydrous THF (125 mL), under an atmosphere of N2, at 0° C. was added NaH (25 mmol, 1.02 g, 60% in mineral oil) and the mixture was stirred for 20 min. To this mixture was added 4-trifluoromethylphenyl isocyanate (4.678 g, 25 mmol) and stirred at 0° C. for 2 h. The mixture was poured into a mixture of ethyl acetate and 2N aq. HCl and the organic phase separated. The organic phase was washed with sodium bicarbonate and brine, dried (MgSO4), filtered and concentrated in vacuo to give a solid. This solid was mixed with ether and filtered to give N′-[4,6-dichloropyrimidin-2-yl]-N-[4-(trifluoromethyl)phenyl]urea (2.6 g, 30% yield): m.p. 99-101° C.; 1H NMR (DMSO-d6) δ 10.78 (bs, 1H), 10.55 (bs, 1H), 7.69 (m, 4H), 7.58 (s, 1H); ESI/MS 348.88 (M−H) 350.97 (M+H).

Workup

  1. stirringstirred at 0° C. for 2 h
  2. customthe organic phase separated
  3. washThe organic phase was washed with sodium bicarbonate and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a solid
  8. filtrationfiltered

Sources & evidence

ORD record
ord-bf5b23bfb911402eab1c6166212bac10
Source dataset
uspto-grants-2011_09
Patent number
US08013154B2

Reaction notes

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