Methyl chloroformate → HCID 54188904, compound

HRID 726342Notes

Reaction equation

HRID 726342 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.Cl[C:19]([O:21][CH3:22])=[O:20]>ClCCl>[CH3:22][O:21][C:19]([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:20]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 226115606-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole

Product 1

HCID 54188904HCID 54188904, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6.0 mg (0.026 mMol) 6-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole and 8.0 mg (.07 mMol) polyvinylpyridine in 3.0 mL dichloromethane were added 2.4 mg (0.0273 mMol) methyl chloroformate. The reaction mixture was mixed for 2 days at ambient temperature. To this mixture were then added 90 mg (0.073 mMol) aminomethylated polystyrene and the reaction mixed for an additional 18 hours. The reaction mixture was then filtered and the volatiles evaporated to give 4.0 mg (53%) of the title compound.

Workup

  1. additionThe reaction mixture was mixed for 2 days at ambient temperature
  2. additionTo this mixture were then added 90 mg (0.073 mMol)
  3. additionthe reaction mixed for an additional 18 hours
  4. filtrationThe reaction mixture was then filtered
  5. customthe volatiles evaporated

Sources & evidence

ORD record
ord-a6b45ba7dc924e39bc7f44bd10ac96cc
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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