Cyanamide → 4-(4-Fluorophenoxy)phenethyl carbamimidate

HRID 705881ノート

反応式

HRID 705881 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[N:18]#[C:19][NH2:20].FC(F)(F)S(O)(=O)=O>C1COCC1>[C:19](=[NH:18])([O:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:10][CH:11]=1)[NH2:20]

参加物

5

反応物 3

HCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677754954-(4-Fluorophenoxy)phenethyl alcohol

生成物 1

HCID 679525344-(4-Fluorophenoxy)phenethyl carbamimidate収率 32.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-{4-[(4-fluorophenyl)oxy]phenyl}ethanol (750 mg, 3.23 mmol) and cyanamide (149 mg, 3.55 mmol) in THF (15 mL) was added trifluoromethanesulfonic acid (0.344 mL, 3.88 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight. After removing the solvent, the residue was diluted with water, extracted with DCM. The organic phase was dried over sodium sulfate, filtered, and concentrated. Purification via reverse phase flash chromatography then afforded the title compound (290 mg, 1.057 mmol, 32.7% yield).

後処理

  1. customAfter removing the solvent
  2. additionthe residue was diluted with water
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via reverse phase flash chromatography

出典と根拠

ORDレコード
ord-8e43322c0f444268bf352fb3cd7e10bb
出典データセット
uspto-grants-2015_11
特許番号
US09174968B2

反応ノート

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