Phenyl chloroformate → HCID 13733130, compound

HRID 1731844Notes

Reaction equation

HRID 1731844 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>C1(C)C=CC=CC=1>[C:24]1([O:23][C:21](=[O:22])[N:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:10][CH:9]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 15137694HCID 15137694, compound

Product 1

HCID 13733130HCID 13733130, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 7.26 g of 6-[[(4-butylphenyl)methyl]amino]-1-hexanol in 50 ml of toluene was added a solution of 2.16 g of phenyl chloroformate in 20 ml of toluene, with the immediate precipitation of a white solid. The resulting mixture was stirred at room temperature for 24 hours. The mixture was filtered, and the filter was washed with toluene. The combined filtrate and wash was evaporated in vacuo and gave a colorless oil. The oil was Kugelrohr distilled and gave 3.5 g of the desired product in 66% yield as a colorless oil, bp 180°-195° C./0.06 mm of mercury.

Workup

  1. customwith the immediate precipitation of a white solid
  2. filtrationThe mixture was filtered
  3. washthe filter was washed with toluene
  4. washThe combined filtrate and wash
  5. customwas evaporated in vacuo
  6. customgave a colorless oil
  7. distillationdistilled

Sources & evidence

ORD record
ord-eb2fcc8c354742358f9f6c2b0e774eae
Source dataset
uspto-grants-1986_11
Patent number
US04623662

Reaction notes

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