Hydrochloric Acid → HCID 68500203, compound

HRID 547552Notes

Reaction equation

HRID 547552 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4](Cl)[N:3]=1.[N+:10]([C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16])([O-:12])=[O:11].Cl>C(OCCO)C.[Cl-].[Na+].O.O>[CH3:8][C:6]1[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=2)[CH:5]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 74233-NitroanilineHCID 218102-Amino-4-chloro-6-methylpyrimidine

Product 1

HCID 68500203HCID 68500203, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 2-amino-4-chloro-6-methyl-pyrimidine (A8) [10.04 g, 69.93 mmol] and 3-nitroaniline 99.95 g, 72.02 mmol) in 2-ethoxyethanol (300 mL) was added c.HCl (30 mL), and the resulting solution was refluxed for ˜16 h. After this time, the reaction mixture was allowed to cool to room temperature, and then diluted with brine and H2O. The resulting suspension was filtered through a Celite pad, and the solid material thus collected re-dissolved in MeOH, and filtered through a pad of Celite. Solvent was removed under reduced pressure to give diamine E1 as an amorphous beige solid, which was used without further purification: 1H NMR (400 MHz, DMSO): δ 12.97 (br s, 1H, pyrimidinyl-N+—H), 11.03 (s, 1H, ArNHAr), 8.52 (s, 1H, ArH), 8.31 (d, J=7.83 Hz, 1H, ArH), 7.97 (ddd, J=8.20, 2.19, 0.72 Hz, 1H, ArH), 7.83 (v br s, 2H, ArNH2), 7.66 (t, J=8.21 Hz, 1H, ArH), 6.25 (s, 1H, ArH), 2.31 (s, 3H, ArCH3); LCMS (APCI+): 246 (100%).

Workup

  1. additionwas added c
  2. filtrationThe resulting suspension was filtered through a Celite pad
  3. customthe solid material thus collected
  4. dissolutionre-dissolved in MeOH
  5. filtrationfiltered through a pad of Celite
  6. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1484644afb754928b1c89b2f36148c68
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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