Methane → HCID 178432423、化合物

HRID 2268745ノート

反応式

HRID 2268745 の反応式
[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]=[C:6](F)[NH:5][C:4]=2[CH:3]=1.Cl.[CH3:15][C:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C.C>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]=[C:6]([NH:22][C:16]3([CH3:15])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[NH:5][C:4]=2[CH:3]=1

参加物

7

反応物 4

HCID 297MethaneHCID 8471TriethylamineHCID 3021577(1-Methylcyclohexyl)amine hydrochlorideHCID 109226916-Chloro-3-fluoro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide

生成物 1

HCID 178432423HCID 178432423、化合物収率 8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 6-chloro-3-fluoro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (0.5 g, 2.08 mmol), 1-methylcyclohexylamine hydrochloride (373 mg, 2.49 mmol) and triethylamine (0.58 ml, 4.16 mmol) in ethanol (3 ml) was stirred for 20 h at 50° C. and then for 22 h at 100° C. in a sealed flask. The cooled mixture was concentrated in vacuo and the residue was triturated with water followed by adjustment to pH <2 with 4M hydrochloric acid. The crude product was isolated by filtration and dissolved in 1 N sodium hydroxide followed by treatment with decolourising charcoal. After filtration, the solution was acidified to pH <2 with 4M hydrochloric acid and the precipitate was filtered off and purified by chromatography (dichloromethane/methanol (19:1)). Recrystallisation from ethanol afforded 55 mg (8%) of the pure title compound; mp 218-219° C.; 1H-NMR (DMSO-d6): δ1.18-1.54 (m, 11H), 1.97-2.12 (m, 2H), 6.55 (br s, 1H), 7.12 (s, 1H), 10.60 (br s, 1H).

後処理

  1. waitfor 22 h at 100° C. in a sealed flask
  2. concentrationThe cooled mixture was concentrated in vacuo
  3. customthe residue was triturated with water
  4. customThe crude product was isolated by filtration
  5. filtrationAfter filtration
  6. filtrationthe precipitate was filtered off
  7. custompurified by chromatography (dichloromethane/methanol (19:1))
  8. customRecrystallisation from ethanol

出典と根拠

ORDレコード
ord-722892babcab491890211558bc0a25b5
出典データセット
uspto-grants-2001_12
特許番号
US06329367B1

反応ノート

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