Ethyl chloroformate → Methyl(1,3,4,9-tetrahydro-2H-carbazol-2-yl)carbamic acid, ethyl ester

HRID 66792Notes

Reaction equation

HRID 66792 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:15][CH2:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH2:4]1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][N:2]([CH:3]1[CH2:15][CH2:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH2:4]1)[C:17](=[O:18])[O:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 20529239HCID 20529239, compound

Product 1

HCID 86737531Methyl(1,3,4,9-tetrahydro-2H-carbazol-2-yl)carbamic acid, ethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 0.05 mol of 2,3,4,9-tetrahydro-N-methyl-1H-carbazol-2-amine in 450 ml of CH2Cl2 and 185 ml of saturated aqueous NaHCO3 was stirred vigorously at room temperature and treated dropwise during 30 min with a solution of 0.15 mol of ethyl chloroformate in an equal volume of CH2Cl2. After stirring vigorously for 5 hr, the CH2Cl2 layer was separated, washed in succession with 10% aqueous K2CO3, H2O, 0.1 N hydrochloric acid, H2O, and dried over anhydrous Na2SO4. The residue remaining after evaporation of the CH2Cl2 was recrystallized from ethanol to give the title compound, mp 167°-168°.

Workup

  1. customthe CH2Cl2 layer was separated
  2. washwashed in succession with 10% aqueous K2CO3, H2O, 0.1 N hydrochloric acid, H2O
  3. dry with materialdried over anhydrous Na2SO4
  4. customafter evaporation of the CH2Cl2
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-d70bb1743c8b40a3845989153f766130
Source dataset
uspto-grants-1982_08
Patent number
US04343812

Reaction notes

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