Triethylamine → 1-(N-Formyl-N-phenylamino)methyl-5-chloropyrimidin-2-one

HRID 1982570Notes

Reaction equation

HRID 1982570 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.C(N(CC)CC)C.Cl[CH2:18][N:19]([CH:26]=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH:26]([N:19]([CH2:18][N:5]1[CH:4]=[C:3]([Cl:2])[CH:8]=[N:7][C:6]1=[O:9])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11126692HCID 11126692, compoundHCID 126485235-Chloropyrimidin-2-ol hydrochloride

Product 1

HCID 156504881-(N-Formyl-N-phenylamino)methyl-5-chloropyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

5-Chloropyrimidin-2-one hydrochloride (3.0 mmol) and triethylamine (6 mmol) were stirred together in CH2Cl2 (50 ml) for 15 minutes before a solution of N-chloromethylformanilide (see Prepartion 12) (3 mmol) in CH2Cl2 was added. The mixture was stirred at 40° C. for 18 hours before the solvent was distilled off. The residue was washed with water and ether. Yield: 0.79 g (50%), m. p. 200° C. (EtOH). 1H NMR (DMSO-d6, δ): 5.68 (s, CH2), 7.32 (Ph), 8.05-8.65 (CHO, H-4 and H-6). IR (KBr, cm-1): 1660 (CO), 1680 (CO). MS (70 eV, m/e (% rel. int.)): 263 (M+, 1), 143 (7), 134 (41), 116 (6), 107 (6), 106 (100), 105 (57), 104 (10), 79 (10), 78 (7), 77 (41), 52 (11), 51 (20).

Workup

  1. additionwas added
  2. distillationwas distilled off
  3. washThe residue was washed with water and ether

Sources & evidence

ORD record
ord-c336675639884cfe9aaadd4bec0f5042
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Reaction notes

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