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Sodium Chloride → isopropyl N-(3-phenylbenzyl)carbamate

HRID 1168029
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HRID 1168029 반응식
Br[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][NH:6][C:7](=[O:12])[O:8][CH:9]([CH3:11])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+].[C:22]1(OB(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[Na+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:22]1([C:2]2[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=2)[CH2:5][NH:6][C:7](=[O:12])[O:8][CH:9]([CH3:11])[CH3:10])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 12090304isopropyl N-(3-bromobenzyl)carbamate

생성물 1

HCID 12090303isopropyl N-(3-phenylbenzyl)carbamate수율 80.6%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 1140Toluene용매

실험 절차

1.20 g of isopropyl N-(3-bromobenzyl)carbamate, 0.47 g of sodium carbonate in aqueous solution (20 ml) and 0.10 g of tetrakis(triphenylphosphine)palladium (0) were added to toluene (40 ml) under a nitrogen atmosphere. The resulting solution was mixed with 0.54 g of phenylboric acid in ethanol (20 ml) at room temperature with stirring and refluxed under heating for 2 hours. After the reaction, the reaction solution was cooled to room temperature, poured into saturated aqueous sodium chloride and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure for removal of the solvent. The residue was purified by silica gel column chromatography to give 0.85 g of isopropyl N-(3-phenylbenzyl)carbamate as white crystals. m.p. 61-64° C.

후처리

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours
  3. customAfter the reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure for removal of the solvent
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-eddd0fd4e55141ddb28bd22f323e9615
출처 데이터셋
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06620961B1

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