Methylamine → 3-iodo-N-methylbenzamide

HRID 238155

반응식

HRID 238155 반응식
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH3:11][NH2:12].C1COCC1>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:12][CH3:11])=[O:6]

참가 물질

5

반응물 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 743783-Iodobenzoyl chloride

생성물 1

HCID 33843663-iodo-N-methylbenzamide수율 26%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cooled (0° C.) solution of 3-iodobenzoyl chloride (2.66 g; 10.0 mmol) in DCM (10 mL) was slowly added a 2 M solution of methylamine in THF (10 mL, 2.0 eq.). Upon completion of the addition, the ice bath was removed and the mixture was stirred overnight. All volatiles were removed in vacuo and the residue was treated with aq. NaHCO3 (25 mL) and subsequently extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel to give the desired 3-iodo-N-methylbenzamide (0.67 g, 26% yield).

후처리

  1. additionUpon completion of the addition
  2. customthe ice bath was removed
  3. customAll volatiles were removed in vacuo
  4. additionthe residue was treated with aq. NaHCO3 (25 mL)
  5. extractionsubsequently extracted with ethyl acetate (3×15 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customevaporated
  8. customThe crude product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-830e194d6d7744bfa5c1b01df3bebe8a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642611B2

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