Hydrochloric Acid → (3,4-Dichlorophenyl)(oxazol-5-yl)methanamine hydrochloride

HRID 715058ノート

反応式

HRID 715058 の反応式
CC(S(/[N:7]=[CH:8]/[C:9]1[O:13][CH:12]=[N:11][CH:10]=1)=O)(C)C.[Cl:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[CH:19][C:20]=1[Cl:21].[Cl-].[NH4+].Cl.O1CCOCC1>CCOCC.C1(C)C=CC=CC=1>[ClH:14].[Cl:14][C:15]1[CH:16]=[C:17]([CH:8]([C:9]2[O:13][CH:12]=[N:11][CH:10]=2)[NH2:7])[CH:18]=[CH:19][C:20]=1[Cl:21]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 312751,4-DioxaneHCID 88924920HCID 88924920、化合物HCID 178478192HCID 178478192、化合物

生成物 1

HCID 68294638(3,4-Dichlorophenyl)(oxazol-5-yl)methanamine hydrochloride収率 97.8%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

A dried-flask was charged with 20 (1.211 g, 6.047 mmol) and toluene (5 mL) was added. The reaction was stirred under nitrogen, cooled to −78° C. and (3,4-dichlorophenyl)magnesium bromide (18.14 mL, 9.071 mmol, 0.5M in THF) was added. The reaction was then warmed to −10° C. for 15 min. Saturated ammonium chloride was added and the reaction was extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was dissolved in DCM (10 mL) then 4 N HCl in dioxane (15.12 mL, 60.47 mmol) was added and the solution was stirred for 30 min. The reaction mixture was added dropwise to a stirred solution of ether. The resulting solid was filtered and washed with ether to afford 1.24 g (73.3%) of (3,4-dichlorophenyl)(oxazol-5-yl)methanamine hydrochloride (22).

後処理

  1. additionwas added
  2. temperatureThe reaction was then warmed to −10° C. for 15 min
  3. extractionthe reaction was extracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe resulting residue was dissolved in DCM (10 mL)
  9. stirringthe solution was stirred for 30 min
  10. filtrationThe resulting solid was filtered
  11. washwashed with ether

出典と根拠

ORDレコード
ord-c504fd30eb1b4b0e8ce455356b245496
出典データセット
uspto-grants-2015_11
特許番号
US09187462B2

反応ノート

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