Sodium borohydride → 6-chloro-N-2-thiazolyl-3-pyridinemethanamine

HRID 1038870ノート

反応式

HRID 1038870 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[N:9][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydride2 回HCID 86649151N-[(6-chloro-3-pyridinyl)methylene]-2-thiazolamine

生成物 1

HCID 44221066-chloro-N-2-thiazolyl-3-pyridinemethanamine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

N-[(6-chloro-3-pyridinyl)methylene]-2-thiazolamine (i.e. the product of Step A) (0.55 g, 2.46 mmol) was added portionwise to a stirred excess of sodium borohydride (0.45 g, 11.8 mmol) in methanol (30 mL). Additional portions of sodium borohydride (2×1 equivalent) were added during the addition of the imine to maintain an exothermic reaction. After addition was complete, the reaction mixture was allowed to stir for 5 min at ambient temperature. The excess reducing agent was quenched by adding glacial acetic acid until gas evolution ceased. The clear reaction mixture was concentrated, and the resulting residue was partitioned between saturated aqueous sodium carbonate and ethyl acetate. The aqueous phase was extracted with ethyl acetate (3×30 mL), and the combined organic phases were washed with brine, dried (MgSO4) and concentrated to give the title compound as a tan powder (0.55 g).

後処理

  1. temperatureto maintain
  2. customan exothermic reaction
  3. additionAfter addition
  4. customwas quenched
  5. additionby adding glacial acetic acid until gas evolution
  6. concentrationThe clear reaction mixture was concentrated
  7. customthe resulting residue was partitioned between saturated aqueous sodium carbonate and ethyl acetate
  8. extractionThe aqueous phase was extracted with ethyl acetate (3×30 mL)
  9. washthe combined organic phases were washed with brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-de2fef16c8ce4c9c8988f896bf381ed6
出典データセット
uspto-grants-2013_10
特許番号
US08552007B2

反応ノート

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