Water → 1H-Benzimidazole, 5-nitro-2-(trichloromethyl)-

HRID 56616

반응식

HRID 56616 반응식
[Cl:1][C:2]([Cl:8])([Cl:7])[C:3](=[NH:6])OC.[N+:9]([C:12]1[CH:13]=[C:14](N)[C:15]([NH2:18])=[CH:16][CH:17]=1)([O-:11])=[O:10].O.C(OCC)(=O)C>C(O)(=O)C>[N+:9]([C:12]1[CH:17]=[CH:16][C:15]2[N:18]=[C:3]([C:2]([Cl:8])([Cl:7])[Cl:1])[NH:6][C:14]=2[CH:13]=1)([O-:11])=[O:10]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 100479Methyl 2,2,2-trichloroacetimidateHCID 51117914-Nitro-1,2-phenylenediamine

생성물 1

HCID 41505451H-Benzimidazole, 5-nitro-2-(trichloromethyl)-

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

At 0° C., 6.3 g (35.9 mmol, 1.1 eq.) of methyl 2,2,2-trichloroethaneimidoate were added dropwise to a solution of 5.0 g (32.7 mmol) of 4-nitrobenzene-1,2-diamine in 150 ml of glacial acetic acid. The reaction mixture was stirred at RT for 3 h and then added to 400 ml of water, and 300 ml of ethyl acetate were added. After phase separation, the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed twice with in each case 130 ml of saturated aqueous sodium bicarbonate solution and once with saturated aqueous sodium chloride solution, dried (sodium sulphate), filtered and concentrated under reduced pressure and dried. The crude product was triturated with pentane and left to stand overnight. The solid was then filtered off, washed with pentane and dried under reduced pressure. Yield: 10.1 g (purity 77%, 85% of theory)

후처리

  1. additionwere added
  2. customAfter phase separation
  3. extractionthe aqueous phase was extracted twice with ethyl acetate
  4. washThe combined organic phases were washed twice with in each case 130 ml of saturated aqueous sodium bicarbonate solution and once with saturated aqueous sodium chloride solution
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customdried
  9. customThe crude product was triturated with pentane
  10. waitleft
  11. waitto stand overnight
  12. filtrationThe solid was then filtered off
  13. washwashed with pentane
  14. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-b54339c0c05b40c2ba60f89e18134946
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434690B2

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