Diethylcarbamoyl chloride → HCID 58444338, compound

HRID 1851661Notes

Reaction equation

HRID 1851661 reaction equation
O.[Na].[CH:3]1[C:16]2[C:7](=[CH:8][C:9]3[C:14]([C:15]=2[CH2:17][OH:18])=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=1.[CH2:19]([N:21]([CH2:25][CH3:26])[C:22](Cl)=[O:23])[CH3:20].CCCCCC>O1CCCC1>[CH2:19]([N:21]([CH2:25][CH3:26])[C:22](=[O:23])[O:18][CH2:17][C:15]1[C:14]2[C:9]([CH:8]=[C:7]3[C:16]=1[CH:3]=[CH:4][CH:5]=[CH:6]3)=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:20]

Participants

6

Reactant 4

HCID 6916Diethylcarbamoyl chlorideHCID 8058HexaneHCID 738489-AnthracenemethanolHCID 71353970Sodium monohydrate

Product 1

HCID 58444338HCID 58444338, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

To the solution containing 1.6 g of 50% sodium hydrate (33 mmol) and 4 mL of dehydrated tetrahydrofuran (dehydrated THF), the solution dissolved 6.3 g of 9-anthracenemethanol (30 mmol; produced by Wako Pure Chemical Industries, Ltd.) into 26 mL of dehydrated tetrahydrofuran (dehydrated THF) was dropped. Then, after this solution of 4.5 g of N,N-diethylcarbamoyl chloride (33 mmol; produced by Sigma-Aldrich Japan Co.) in 4 mL of dehydrated tetrahydrofuran (dehydrated THF) was added, the solution was reacted by stirring for 2 hours at 60° C. After completing reaction, reaction solution was cooled, and n-hexane was poured into the cooled solution, then, the solution was washed with water, and organic layer after washing was condensed. The resultant condensed residue was purified with column chromatography (Filler: Silica-Gel (Wako-Gel C-200; produced by Wako Pure Chemical Industries, Ltd.), Developing solvent: n-heptane) to obtain 5.7 g of 9-anthrylmethyl N,N-diethylcarbamate (yield: 61%) represented by the above-described formula [7] as yellow crystal. Measurement results of 1H-NMR and melting point are shown as the follows:

Workup

  1. additionwas dropped
  2. customthe solution was reacted
  3. customreaction, reaction solution
  4. temperaturewas cooled
  5. washthe solution was washed with water, and organic layer
  6. washafter washing
  7. customcondensed
  8. customThe resultant condensed residue
  9. customwas purified with column chromatography (Filler: Silica-Gel (Wako-Gel C-200; produced by Wako Pure Chemical Industries, Ltd.), Developing solvent: n-heptane)

Sources & evidence

ORD record
ord-ab3e97b154614c7ea44abd612879bccd
Source dataset
uspto-grants-2015_02
Patent number
US08957212B2

Reaction notes

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