Hydrochloric Acid → HCID 22978795, compound

HRID 1851663Notes

Reaction equation

HRID 1851663 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][OH:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH:17]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.Cl.CN(C)[CH:27]=[O:28]>>[CH:17]1([NH:23][C:27](=[O:28])[O:16][CH2:15][C:13]2[C:12]3[C:7]([CH:6]=[C:5]4[C:14]=2[CH:1]=[CH:2][CH:3]=[CH:4]4)=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 7965CyclohexylamineHCID 738489-Anthracenemethanol

Product 1

HCID 22978795HCID 22978795, compoundYield 92%

Procedure

To the solution dissolved 8.92 g of N,N′-carbonyldiimidazole (55 mmol; produced by Wako Pure Chemical Industries, Ltd.) into 40 mL of dimethylformamide (DMF), 10.4 g of 9-anthracenemethanol (50 mmol; produced by Wako Pure Chemical Industries, Ltd.) was added under cooling with ice, then, the solution was reacted by stirring for 1 hour at the same temperature. Subsequently, 6.94 g of monocyclohexylamine (70 mmol; produced by Wako Pure Chemical Industries, Ltd.) was added to this solution, and the solution was reacted by stirring for 2 hours at room temperature. After completing reaction, the reaction solution was poured into 110 mL of 3.5% hydrochloric acid, the resultant crystal was filtered, then, the resultant crystal was dried, the crystal after drying was added to 100 mL of toluene, and was hot-dissolved to hot-filtered at the temperature of 100° C. Subsequently, the filtrate obtained by filtration was cooled with ice, and the precipitated crystal was filtered, then, the resultant crystal was dried to obtain 15.4 g of 9-anthrylmethyl N-cyclohexylcarbamate (yield: 92%) represented by the above-described formula [15] as yellow crystal. Measurement results of 1H-NMR and melting point are shown as the follows:

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. customthe solution was reacted
  4. customthe solution was reacted
  5. stirringby stirring for 2 hours at room temperature
  6. customreaction
  7. filtrationthe resultant crystal was filtered
  8. customthe resultant crystal was dried
  9. customthe crystal after drying
  10. additionwas added to 100 mL of toluene
  11. dissolutionwas hot-dissolved
  12. filtrationto hot-filtered at the temperature of 100° C
  13. customSubsequently, the filtrate obtained by filtration
  14. temperaturewas cooled with ice
  15. filtrationthe precipitated crystal was filtered
  16. customthe resultant crystal was dried

Sources & evidence

ORD record
ord-43306e4345f3427b84ba0221cde53e0c
Source dataset
uspto-grants-2015_02
Patent number
US08957212B2

Reaction notes

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