Methyl chloroformate → HCID 54188904, compound

HRID 843892Notes

Reaction equation

HRID 843892 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 (0.07 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-e14d71cf968d4256ae268100c0b86628
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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