Ethyl isocyanate → HCID 54539808, compound

HRID 894465Notes

Reaction equation

HRID 894465 reaction equation
[Cl:1][C:2]1[C:19]([OH:20])=[CH:18][C:5]2[C@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][N:8]([CH3:11])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[CH2:21]([N:23]=[C:24]=[O:25])[CH3:22]>C(#N)C>[Cl:1][C:2]1[C:19]([O:20][C:24]([NH:23][CH2:21][CH3:22])=[O:25])=[CH:18][C:5]2[C@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][N:8]([CH3:11])[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 6603800(5S)-8-Chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl-1H-3-benzazepin-7-ol

Product 1

HCID 54539808HCID 54539808, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dissolve 1.22 g (0.0042 moles) of the product of step E in 60 ml of refluxing acetonitrile and add dropwise 0.6 ml of ethyl isocyanate with stirring. Reflux for 30 minutes after addition is complete. Evaporate to dryness and crystallize the residue from acetonitrile to obtain analytically pure (S)-7-chloro-8-(ethylaminocarbonyloxy)-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 133°-134.5° C. [α]D26 =+20.2° (c=0.5, ethanol).

Workup

  1. temperatureReflux for 30 minutes
  2. additionafter addition
  3. customEvaporate to dryness
  4. customcrystallize the residue from acetonitrile

Sources & evidence

ORD record
ord-12c8355f12324f1eaf822af12244354c
Source dataset
uspto-grants-1981_08
Patent number
US04284555

Reaction notes

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