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N-(3-Chlorophenyl)acetamide → N-[3-(Dibutylamino)phenyl]acetamide

HRID 1354980
ノート
印刷プレビュー

反応式

HRID 1354980 の反応式
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Cl)[CH:6]=1)=[O:3].C[C:13]([CH3:16])([O-])[CH3:14].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[CH2:5]([N:4]([CH2:2][CH2:14][CH2:13][CH3:16])[C:7]1[CH:6]=[C:5]([NH:4][C:2](=[O:3])[CH3:1])[CH:10]=[CH:9][CH:8]=1)[CH2:6][CH2:7][CH3:8]
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 2

HCID 11493N-(3-Chlorophenyl)acetamideHCID 23676156Sodium t-butoxide

生成物 1

HCID 13879300N-[3-(Dibutylamino)phenyl]acetamide収率 161.6%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl触媒

実験手順

An oven-dried resealable schlenk tube containing a stir bar was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (11.9 mg, 0.025 mmol), 3-chloroacetanilide (85 mg, 0.5 mmol) and sodium tbutoxide (120 mg, 1.25 mmol). The tube was capped with a rubber septum, evacuated and backfilled with argon. Dinbutylamine (126 μL, 0.75 mmol) and tbutanol (1 mL) were added through the septum via syringe. The septum was replaced with a Teflon screw cap. The schlenk tube was sealed and put into a pre-heated oil bath at 90° C. The reaction mixture was stirred for 18 h, allowed to cool down to room temperature and quenched with water. Extraction with ethyl acetate three times followed by chromatography on silica gel column with 4:1 hexane:ethyl acetate gave 106 mg (81%) of the title compound as a pale yellow oil.

後処理

  1. additionAn oven-dried resealable schlenk tube containing a stir bar
  2. customThe tube was capped with a rubber septum
  3. customevacuated
  4. additionDinbutylamine (126 μL, 0.75 mmol) and tbutanol (1 mL) were added through the septum via syringe
  5. customscrew cap
  6. customThe schlenk tube was sealed
  7. customput into a pre-heated oil bath at 90° C
  8. customquenched with water
  9. extractionExtraction with ethyl acetate three times

出典と根拠

ORDレコード
ord-5e83fbd8bb524de3bab2ce767bba3562
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07223879B2

反応ノート

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