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Ammonia → HCID 19348480, 화합물

HRID 1418194
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HRID 1418194 반응식
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])([CH3:4])([CH3:3])[CH3:2].[NH3:17].C(OCC)(=O)C.CCCCCC>C(#N)C.C(OCC)(=O)C.CCCCCC>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](=[O:10])[NH2:17])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 8058HexaneHCID 8857Ethyl AcetateHCID 7388134-Tert-butyl-3-nitrobenzoic acid

생성물 1

HCID 19348480HCID 19348480, 화합물수율 85%

시약·촉매·용매 2

HCID 6342Acetonitrile용매
HCID 21226206
Ethyl acetate hexane
용매

실험 절차

12.0 g (74.0 mmol) of N,N'-carbonyldiimidazole were added to a suspension of 15.03 g (67.3 mmol) of 4-t-butyl-3-nitrobenzoic acid in 150 ml of acetonitrile, and the resulting mixture was stirred for 1 hour, after which 20 ml (0.31 mol) of aqueous ammonia were added. The reaction mixture was stirred for 30 minutes, after which it was concentrated by evaporation under reduced pressure, and the concentrate was dissolved in ethyl acetate. The organic phase was washed with water, with 2N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 150 g of silica gel, using a gradient elution method, with mixtures of ethyl acetate and hexane ranging from 1:1 to 2:1 by volume as the eluent, to give 12.68 g (yield 85%) of the title compound as crystals, melting at 114°-115° C. (from ethyl acetate-hexane).

후처리

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. concentrationafter which it was concentrated by evaporation under reduced pressure
  3. dissolutionthe concentrate was dissolved in ethyl acetate
  4. washThe organic phase was washed with water, with 2N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialafter which it was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through 150 g of silica gel
  8. washa gradient elution method

출처 및 근거

ORD 기록
ord-ea541de061ea4c2781ff3dee86bdf6c1
출처 데이터셋
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05880147

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