1,2-Dichloroethane → 5-bromo-N,N-diethyl-2-hydroxybenzamide

HRID 1970262ノート

反応式

HRID 1970262 の反応式
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Br:6][C:7]1[CH:15]=[C:11]([C:12]([OH:14])=O)[C:10]([OH:16])=[CH:9][CH:8]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([OH:16])=[C:11]([CH:15]=1)[C:12]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:14]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 69725-Bromosalicylic acidHCID 8021DiethylamineHCID 181649HOAt

生成物 1

HCID 242852955-bromo-N,N-diethyl-2-hydroxybenzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Diethylamine (2.39 mL, 23.0 mmol) was added to a solution of 5-bromosalicylic acid (1.000 g, 4.61 mmol), EDC (1.33 g, 6.91 mmol), HOAt (0.627 g, 4.61 mmol) and DMF (20.0 mL) and the system was flushed with argon. The tube was sealed and the mixture stirred at 50° C. for 12 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a brown oil. This oil was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% ethyl acetate-hexane) to afford 5-bromo-N,N-diethyl-2-hydroxybenzamide as an off-white solid. MS m/z=272.1, 274.1 [M+H]+. Calcd for C11H14BrNO2: 272.1.

後処理

  1. customthe system was flushed with argon
  2. customThe tube was sealed
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford a brown oil
  11. customThis oil was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-b18d29ca88ca4e7a9a4d179899743626
出典データセット
uspto-grants-2013_04
特許番号
US08426447B2

反応ノート

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