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Dimethylformamide → HCID 22344577、化合物

HRID 2299736
ノート
印刷プレビュー

反応式

HRID 2299736 の反応式
C(Cl)(=O)C(Cl)=O.C[N:8](C)[CH:9]=[O:10].[O:12]=[C:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:14][CH2:15][CH2:16][CH2:17]C(O)=O>O1CCCC1>[O:12]=[C:13]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:14][CH2:15][CH2:16][CH2:17][C:9]([NH2:8])=[O:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2235955-Benzoylpentanoic Acid

生成物 1

HCID 22344577HCID 22344577、化合物収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Oxalyl chloride (0.508 ml) and N,N-dimethylformamide (catalytic amount) were added to a solution of 6-oxo-6-phenylhexanoic acid (1.00 g) in tetrahydrofuran (15 ml) at room temperature, which was stirred at room temperature for 1 hour and concentrated. The residue was dissolved in ethyl acetate (25 ml) and added dropwise to a stirred mixture of 25% aqueous ammonia (20 ml) and ethyl acetate (25 ml) at 0° C. After stirring at room temperature for 2 hours, water (200 ml) was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The remaining crystals were recrystallized from ethyl acetate-hexane to obtain 6-oxo-6-phenylhexanamide (885 mg, yield 89%) as colorless crystals. m.p. 113-114° C.

後処理

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (25 ml)
  3. additionadded dropwise to a stirred mixture of 25% aqueous ammonia (20 ml) and ethyl acetate (25 ml) at 0° C
  4. stirringAfter stirring at room temperature for 2 hours
  5. additionwater (200 ml) was added
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe remaining crystals were recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-0e52c439873b4268a32b30f7026b75e5
出典データセット
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06495581B1

反応ノート

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