Hydrochloric Acid → 6-[(1,1-Dimethylethyl)thio]-3-pyridinemethanamine

HRID 2041509ノート

反応式

HRID 2041509 の反応式
[C:1]([S:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C1COCC1.CO>[NH2:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:7][CH:8]=1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 284131906-(Tert-butylsulfanyl)pyridine-3-carbonitrile

生成物 1

HCID 435287746-[(1,1-Dimethylethyl)thio]-3-pyridinemethanamine収率 61.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Use a method similar to the General Procedure 6-5 to react 6-(tert-butylthio)nicotinonitrile (4.4 g, 22.7 mmol) in anhydrous THF (25 mL) with 1M BH3-THF complex in THF (25 mL, 25 mmol). Add 5M aqueous HCl (10 mL) cautiously and stir the mixture overnight at room temperature. Extract into EtOAc, wash with brine, dry over MgSO4 and concentrate in vacuo to give an orange solid. Dissolve the crude mixture in methanol and filter through an SCX column eluting with methanol followed by 3M ammonia in methanol to obtain the title compound (2.74 g, 61%). MS (ES+) m/z: 197 (M+H)+.

後処理

  1. extractionExtract into EtOAc
  2. washwash with brine
  3. dry with materialdry over MgSO4
  4. concentrationconcentrate in vacuo
  5. customto give an orange solid
  6. filtrationfilter through an SCX column
  7. washeluting with methanol

出典と根拠

ORDレコード
ord-9398ab867daa4b84b0161aeff82f1573
出典データセット
uspto-grants-2013_11
特許番号
US08580780B2

反応ノート

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