Ethyl chloroformate → HCID 70574908, compound

HRID 1680491Notes

Reaction equation

HRID 1680491 reaction equation
Cl[C:2]([O:4][CH2:5]C)=[O:3].[NH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)=[CH:11]1>N1C=CC=CC=1>[CH3:5][O:4][C:2]([NH:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C:20]2[NH:24][CH:23]=[CH:22][N:21]=2)=[CH:11]1)=[O:3]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 70574771HCID 70574771, compound

Product 1

HCID 70574908HCID 70574908, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl chloroformate (0.19 g) was added dropwise to a stirred solution of 1-(2-aminoethyl)-3-(1-imidazolylmethyl)indole (0.48 g) in pyridine (5 ml) at room temperature. The solution was stirred at room temperature for 3 hours and then evaporated. The residue was stirred with aqueous sodium bicarbonate solution and the solid product was filtered off, washed with water, dried and crystallised from ethyl acetate/petrol (b.p. 60°-80° C.) to give 1-(2-methoxycarbonylaminoethyl)3-(1-imidazolylmethyl)indole (0.32 g), m.p. 78°-79° C. Found: C, 62.22; H, 5.99; N, 17.72. C16H18N4O2.1/2H2O requires: C, 62.52; H, 6.23; N, 18.23%.

Workup

  1. customevaporated
  2. stirringThe residue was stirred with aqueous sodium bicarbonate solution
  3. filtrationthe solid product was filtered off
  4. washwashed with water
  5. customdried
  6. customcrystallised from ethyl acetate/petrol (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-4c09f2ae6cd6465bb0407c8268a1f813
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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