Ethyl isocyanate → HCID 54027157, compound

HRID 726348Notes

Reaction equation

HRID 726348 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([N:15]([CH3:17])[CH3:16])[CH2:6][C:5]2=1.[CH2:18]([N:20]=[C:21]=[O:22])[CH3:19]>ClCCl>[CH2:18]([NH:20][C:21]([NH:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([N:15]([CH3:17])[CH3:16])[CH2:6][C:5]2=1)=[O:22])[CH3:19]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 226115606-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole

Product 1

HCID 54027157HCID 54027157, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10.0 mg (0.0437 mMol) 6-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole in 3.0 mL dichloromethane were added 6.2 mg (0.0874 mMol) ethyl isocyanate. The reaction was mixed for 48 hours and to it were then added 0.15 gm (0.0874 mMol) aminomethylated polystyrene and the reaction mixed for an additional 18 hours. The reaction mixture was then filtered and the filtrate washed with 1N hydrochloric acid. The aqueous phase was washed several times with dichloromethane and was then made basic with dilute aqueous sodium hydroxide. The aqueous phase was then extracted several times with an equal volume of dichloromethane. These organic extracts were dried over sodium sulfate and then concentrated under reduced pressure to give 3.0 mg (23%) of the title compound.

Workup

  1. additionThe reaction was mixed for 48 hours and to it
  2. additionwere then added 0.15 gm (0.0874 mMol)
  3. additionthe reaction mixed for an additional 18 hours
  4. filtrationThe reaction mixture was then filtered
  5. washthe filtrate washed with 1N hydrochloric acid
  6. washThe aqueous phase was washed several times with dichloromethane
  7. extractionThe aqueous phase was then extracted several times with an equal volume of dichloromethane
  8. dry with materialThese organic extracts were dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1cc9b1983c494ebe8532b0edc632af03
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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