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

HRID 247085Notes

Reaction equation

HRID 247085 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]([C:26](=[O:28])[CH3:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[C: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:28])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10655068HCID 10655068, compoundHCID 126485235-Chloropyrimidin-2-ol hydrochloride

Product 1

HCID 201613291-(N-Acetyl-N-phenylamino)methyl-5-chloropyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

5-Chloropyrimidin-2-one hydrochloride (3.8 mmol) and triethylamine (7.6 mmol) was stirred together in CH2Cl2 (30 ml) for 10 minutes before a solution of N-chloromethyl acetanilide (see Preparation 16) (3.8 mmol) in CH2Cl2 (5 ml) was added. The mixture was stirred at 40° C. for 2 hours before the solvent was distilled off and the residue washed with water and ether. Yield 0.3 g, (28%) M.p. 150°-155° C. (decomp) (CH2Cl2 /pet. ether) 1H NMR (CDCl3, δ): 1.90 (CH3), 5.60 (CH2), 6.9-7.4 (Ph), 8.18 and 8.42 (H-4, H-6, J3Hz). IR (KBr) 1670-1680 cm-1 (CO).

Workup

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

Sources & evidence

ORD record
ord-f8f508ddff314afaa2e0b0c3313662f5
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Reaction notes

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