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

HRID 874721노트

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HRID 874721 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

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온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-23e1971d56e841e99c6a58ea4a429f02
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980933B2

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