Hydrochloric Acid → N-Allyl,N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

HRID 1010783ノート

反応式

HRID 1010783 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[I:15])=[O:4].C([O-])([O-])=O.[K+].[K+].[OH-].[K+].[CH2:26](Br)[CH:27]=[CH2:28].Cl>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[CH2:28]([N:5]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[I:15])[C:3](=[O:4])[C:2]([F:16])([F:1])[F:17])[CH:27]=[CH2:26]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 22292821N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

生成物 1

HCID 24773729N-Allyl,N-trifluoroacetyl-2-iodo-4-chlorophenethylamine収率 75.8%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

実験手順

A solution of N-trifluoroacetyl-2-iodo-4-chlorophenethylamine (0.94 g, 2.4 mmol) in toluene (25 mL) was treated with K2CO3 (0.43 g, 3.12 mmol), KOH (0.40 g, 7.2 mmol), n-Bu4NBr (0.077 g, 0.24 mmol) and allyl bromide (0.43 g, 3.6 mmol) sequentially. The mixture was stirred at 80 C for 3.5 hours, cooled to 20 C and acidified with 10% aqueous HCl. The phases were separated, the aqueous phase extracted with ether (100 mL), the combined organic phases were washed with brine (50 mL), dried with Na2SO4 and concentrated to give 0.76 g of a clear oil. MS calculated for C13H12ClF3INO+H: 418, observed: 418.

後処理

  1. temperaturecooled to 20 C
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with ether (100 mL)
  4. washthe combined organic phases were washed with brine (50 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-9c572701d6264b7b9822bbf6ae66a1e7
出典データセット
uspto-grants-2011_07
特許番号
US07977329B2

反応ノート

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