Ethylenediamine → 6-[N'-(2-aminoethyl)thioureido]-1-t-butoxycarbonyl-2,3-dihydro-7-methylindole

HRID 1275652Notes

Reaction equation

HRID 1275652 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N:18]=[C:19]=[S:20])[C:15]=2[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:24])[CH2:22][NH2:23]>C(Cl)Cl>[NH2:23][CH2:22][CH2:21][NH:24][C:19](=[S:20])[NH:18][C:14]1[C:15]([CH3:17])=[C:16]2[C:11]([CH2:10][CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 158963721-t-Butoxycarbonyl-2,3-dihydro-6-isothiocyanato-7-methylindole

Product 1

HCID 158963736-[N'-(2-aminoethyl)thioureido]-1-t-butoxycarbonyl-2,3-dihydro-7-methylindoleYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the above crude 1-t-butoxycarbonyl-2,3-dihydro-6-isothiocyanato-7-methylindole (0.59 g) in methylene chloride (10 mL) is slowly added to a solution of ethylenediamine (0.60 g, 10 mmol) in methylene chloride (10 mL). After 30 minutes, the solution is washed with four 50-mL portions of aqueous potassium carbonate, dried over anhydrous potassium carbonate, filtered and rotary evaporated to yield 6-[N'-(2-aminoethyl)thioureido]-1-t-butoxycarbonyl-2,3-dihydro-7-methylindole as an amber glassy solid (0.72 g). This material is taken on into the next reaction without further purification.

Workup

  1. washthe solution is washed with four 50-mL portions of aqueous potassium carbonate
  2. dry with materialdried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. customrotary evaporated

Sources & evidence

ORD record
ord-14a457f59e834155b943bdc4f62418bf
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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