Potassium Bromide → 1-(3-Tolylsulfenyl)methyl-5-chloropyrimidin-2-one

HRID 1982560

反応式

HRID 1982560 の反応式
CC(C)([O-])C.[K+].Cl.[Cl:8][C:9]1[CH:10]=[N:11][C:12](=[O:15])[NH:13][CH:14]=1.Cl[CH2:17][S:18][C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=1.[K+].[Br-]>CN(C=O)C.C(O)(C)C.CCO>[C:21]1([CH3:25])[CH:22]=[CH:23][CH:24]=[C:19]([S:18][CH2:17][N:11]2[CH:10]=[C:9]([Cl:8])[CH:14]=[N:13][C:12]2=[O:15])[CH:20]=1

参加物

7

反応物 4

HCID 253877Potassium BromideHCID 126485235-Chloropyrimidin-2-ol hydrochlorideHCID 128408943-Methylphenyl chloromethyl sulfideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 135300961-(3-Tolylsulfenyl)methyl-5-chloropyrimidin-2-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒3 回HCID 22179027Isopropanol ethanol溶媒

実験手順

Potassium tert-butoxide (20 mmol) in DMF (12 ml) was added to a solution of 5-chloro-pyrimidin-2-one hydrochloride (10 mmol) in DMF (60 ml). After stirring for 13 min, a solution of 3-chloromethylthiotoluene (10 mmol) in DMF (12 ml) was added. The resultant mixture was stirred at 60° C. for 3 h, the solvent distilled off at reduced pressure and the residue triturated and washed well with water before drying. The product was the N- and O-alkylated isomers in the ratio 7:5; yield: 1.71 g (64%). The N-isomer was isolated by its low solubility in ether in which the O-isomer is readily soluble; m.p. 134° C. (isoPrOH/EtOH). (Found C53.73; H4.25. Calc. for C12H11ClN2OS: C54.03; H4.16) 1H NMR (DMSO-d6): δ 2.27 (Me), 5.22 (CH2), 7.17 (Ph). 8.00 and 8.56 (H-4 and H-6, J 4 Hz). IR (KBr): 1660 cm-1 (CO). MS [70 eV, m/z (% rel. int.)]: 266/268 (6/2,M) 143/145 (100/32). MS [70 eV, m/z (% rel. int.)] : 266/268 (11/4,M, 137 (100).

後処理

  1. distillationthe solvent distilled off at reduced pressure
  2. customthe residue triturated
  3. washwashed well with water
  4. custombefore drying
  5. customThe N-isomer was isolated by its low solubility in ether in which the O-isomer

出典と根拠

ORDレコード
ord-84395e1d1c4946f7bac26af910f047af
出典データセット
uspto-grants-1986_06
特許番号
US04596870

関連ノート

読み込み中…