Ethyl chloroformate → HCID 70431093, compound

HRID 652715Notes

Reaction equation

HRID 652715 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH2:16][CH2:17][NH2:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([O:21][C:22](Cl)=[O:23])[CH3:20].[OH-].[Na+]>C(Cl)Cl.O>[CH2:19]([O:21][C:22](=[O:23])[NH2:9])[CH3:20].[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH2:16][CH2:17][NH2:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 12324024HCID 12324024, compound

Product 1

HCID 70431093HCID 70431093, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 18.9 g 3-phenyl-1H-indol-2-ethanamine in 220 ml methylene chloride are added 15.3 ml of chloroformic ethyl ester followed by 110 ml water. The mixture is stirred for 10 minutes. 6.4 g sodium hydroxide in 100 ml water are added and stirring is continued for further 20 minutes at room temperature. The organic phase is separated, washed once with 2N tartaric acid and water, dried and evaporated under reduced pressure. The oily residue of the heading compound is used without further purification.

Workup

  1. stirringstirring
  2. waitis continued for further 20 minutes at room temperature
  3. customThe organic phase is separated
  4. washwashed once with 2N tartaric acid and water
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe oily residue of the heading compound is used without further purification

Sources & evidence

ORD record
ord-927ccf7a0ef3491188abeb9718b429b9
Source dataset
uspto-grants-1987_06
Patent number
US04673674

Reaction notes

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