Triethylamine → 3-Chloro-4,5-dimethoxyphenyl(tosyl)methyl isocyanide

HRID 874721ノート

反応式

HRID 874721 の反応式
[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([S:7]([CH:10]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([Cl:24])[CH:15]=2)[NH:11][CH:12]=O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.O=P(Cl)(Cl)Cl.C(N(CC)CC)C>C(COC)OC>[Cl:24][C:16]1[CH:15]=[C:14]([CH:10]([N+:11]#[C-:12])[S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:25])=[CH:6][CH:5]=2)(=[O:9])=[O:8])[CH:19]=[C:18]([O:20][CH3:21])[C:17]=1[O:22][CH3:23]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 46938394N-[(Toluene-4-sulfonyl)-(3-chloro-4,5-dimethoxyphenyl)methyl]formamide

生成物 1

HCID 469385023-Chloro-4,5-dimethoxyphenyl(tosyl)methyl isocyanide

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
-10 °C

実験手順

Compound 3a (4.57 g, 11.92 mmol) was suspended in dry dimethoxyethane (100 mL) and cooled to −10° C. POCl3 (3.4 mL, 36.1 mmol) was added and a mixture of triethylamine (8.3 mL, 59.5 mmol) in dimethoxyethane (10 mL) was dropped slowly to the reaction mixture. After stirring for 2 h at −5° C., the reaction mixture was poured into ice water. The aqueous phase was extracted with ethyl acetate, the organic phase was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuum. Upon refrigeration (4° C.) over night a yellow solid crystallized, which was collected and dried in vacuum.

後処理

  1. additionwas dropped slowly to the reaction mixture
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe organic phase was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customUpon refrigeration (4° C.) over night a yellow solid crystallized
  8. customwhich was collected
  9. customdried in vacuum

出典と根拠

ORDレコード
ord-23e1971d56e841e99c6a58ea4a429f02
出典データセット
uspto-grants-2015_03
特許番号
US08980933B2

反応ノート

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