4-(2-(Diethylamino)ethoxy)aniline → HCID 58786791, compound

HRID 1375395Notes

Reaction equation

HRID 1375395 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.[CH2:14]([N:16]([CH2:27][CH3:28])[CH2:17][CH2:18][O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)[CH3:15]>C1COCC1.CC(O)C>[CH2:27]([N:16]([CH2:14][CH3:15])[CH2:17][CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([NH:24][C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=2)=[CH:25][CH:26]=1)[CH3:28]

Participants

5

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 71472332-Chloro-N-ethyl-5-nitro-4-pyrimidinamine

Product 1

HCID 58786791HCID 58786791, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.013 g (5 mmol) of 2-chloro-4-(ethylamino)-5-nitropyrimidine in 50 mL THF at −78° C. is added a solution of 2.48 g (12 mmol) of 4-[2-(diethylamino)ethoxy]aniline in 50 mL of 2-propanol, and the resulting mixture is allowed to warm slowly to room temperature. After removal of the solvent, the residue is dissolved in aqueous acetic acid and filtered through celite. The aqueous solution is then basified with aqueous ammonia, and the resulting precipitate is collected, washed with water, and dried to give 1.65 g (95%) of the title compound: mp (MeOH) 134–136° C.

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue is dissolved in aqueous acetic acid
  3. filtrationfiltered through celite
  4. customthe resulting precipitate is collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b10aa025c2264a759a038646b5ea0ca6
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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