Hydrochloric Acid → HCID 86760840、化合物

HRID 2108509ノート

反応式

HRID 2108509 の反応式
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[I:16])=[O:4].C([O-])([O-])=O.[K+].[K+].[OH-].[K+].[CH2:27](Br)[CH:28]=[CH2:29].Cl>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[CH2:29]([N:5]([CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[I:16])[C:3](=[O:4])[C:2]([F:1])([F:17])[F:18])[CH:28]=[CH2:27]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 222927722,2,2-Trifluoro-N-[2-(2-iodo-5-methoxyphenyl)ethyl]acetamide

生成物 1

HCID 86760840HCID 86760840、化合物収率 77.8%

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-5-methoxyphenethylamine (23.8 g, 63.8 mmol) in toluene (425 mL) was sequentially treated with K2CO3 (12.4 g, 89.8 mmol), KOH (11.6 g, 207 mmol), n-Bu4NBr (2.2 g, 6.9 mmol) and allyl bromide (10.7 g, 89.8 mmol). The mixture was stirred at 80 C for 3.5 hours, cooled to 20 C, acidified with 10% aqueous HCl, separated and the aqueous phase extracted with ether (500 mL). The combined organic phases were washed with brine (200 mL), dried with Na2SO4 and concentrated to give 20.5 g of a brown oil. 1H NMR (400 MHz, CDCl3), mixture of rotamers d 7.67 (m, 1H), 6.80 (m, 1H), 6.57 (m, 1H), 5.9-5.6 (bm, 1H), 5.27 (m, 2H), 4.11 (d, J=6 Hz, 0.5H), 3.85 (d, J=6 Hz, 0.5H), 3.77 (m, 3H), 3.55 (m, 2H), 3.00 (m, 2H). MS calculated for C14H15F3INO2+H: 414, observed: 414.

後処理

  1. temperaturecooled to 20 C
  2. customseparated
  3. extractionthe aqueous phase extracted with ether (500 mL)
  4. washThe combined organic phases were washed with brine (200 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-0c0fb65c8a904de180c7476dae37dfe3
出典データセット
uspto-grants-2009_04
特許番号
US07514422B2

反応ノート

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