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

HRID 1168029
Notes
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Reaction equation

HRID 1168029 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent
HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-eddd0fd4e55141ddb28bd22f323e9615
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06620961B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes