Formamide → {(3-Iodophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide

HRID 32563

反応式

HRID 32563 の反応式
[CH3:1][Si](Cl)(C)C.[I:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=O.[CH:15]([NH2:17])=[O:16].[C:18]1(C)[C:19]([S:24]([OH:26])=[O:25])=[CH:20][CH:21]=[CH:22][CH:23]=1>CC#N.C1(C)C=CC=CC=1.O.COC(C)(C)C>[I:6][C:7]1[CH:8]=[C:9]([CH:10]([NH:17][CH:15]=[O:16])[S:24]([C:19]2[CH:18]=[CH:23][C:22]([CH3:1])=[CH:21][CH:20]=2)(=[O:25])=[O:26])[CH:12]=[CH:13][CH:14]=1

参加物

9

反応物 4

HCID 713FormamideHCID 6397ChlorotrimethylsilaneHCID 2526103-IodobenzaldehydeHCID 126612952-Methylbenzene-1-sulfinic acid

生成物 1

HCID 85929703{(3-Iodophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide収率 51%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
50 °C

実験手順

Trimethylsilylchloride (9.1 mL) was added to a stirred solution of 3-iodobenzaldehyde (15.1 g) and formamide (6.5 mL) in MeCN (34 mL) and toluene (34 mL) under an inert atmosphere. The reaction was then heated at 50° C. for 5 hours. Toluene sulfinic acid (15.3 g) was added and the reaction mixture was heated at 50° C. for a fisher 5 hours. The reaction mixture was cooled to ambient temperature, methyl t-butylether (55 mL) was added and stirred for 5 minutes. Water (275 mL) was added, the reaction cooled to 0° C. and stirred for 1 hour. The solid was filtered and the reaction flask was washed with MTBE (2×35 mL) and poured over the filtered cake. The solid was dried in a vacuum oven at 60° C. for 10 hours to afford impure title compound as a solid (14 g, 51%) which was used without further purification. A small sample was crystallised from EtOH;

後処理

  1. temperaturethe reaction mixture was heated at 50° C. for a fisher 5 hours
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. temperaturethe reaction cooled to 0° C.
  4. stirringstirred for 1 hour
  5. filtrationThe solid was filtered
  6. washthe reaction flask was washed with MTBE (2×35 mL)
  7. additionpoured over the filtered cake
  8. customThe solid was dried in a vacuum oven at 60° C. for 10 hours

出典と根拠

ORDレコード
ord-6f7c7740c4974382bd848d9d695a005a
出典データセット
uspto-grants-2008_09
特許番号
US07427616B2

関連ノート

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