Ethylenediamine → HCID 22461247, compound

HRID 1275661Notes

Reaction equation

HRID 1275661 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[C:7]([CH3:15])[C:8]([N:12]=[C:13]=[S:14])=[CH:9][CH:10]=2)[NH:5][CH:4]=1)#[N:2].[CH2:16]([NH2:19])[CH2:17][NH2:18]>C(Cl)Cl>[C:1]([C:3]1[C:11]2[C:6](=[C:7]([CH3:15])[C:8]([NH:12][C:13]([NH:18][CH2:17][CH2:16][NH2:19])=[S:14])=[CH:9][CH:10]=2)[NH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 22461231HCID 22461231, compound

Product 1

HCID 22461247HCID 22461247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyano-6-isothiocyanato-7-methylindole (0.152 g, 0.713 mmol) in methylene chloride (30 mL) is added ethylenediamine (0.286 mL, 4.28 mmol). The milky white mixture is stirred for 30 minutes followed by removal of the volatile organics by rotary evaporation. The residue is taken up in 10% methanol/methylene chloride, causing a precipitate to form. This mixture is filtered (solid is saved), and the filtrate is directly applied to a silica gel column. The mixture is separated using 15% methanol (ammonium hydroxide treated)/methylene chloride as eluent. The product containing fractions are combined with the previous precipitate and the solvents removed by rotary evaporation to yield 0.214 g of slightly impure 3-cyano-6-[N'-(2-aminoethyl)thioureido]-7-methylindole as a white solid.

Workup

  1. customfollowed by removal of the
  2. customvolatile organics by rotary evaporation
  3. customto form
  4. filtrationThis mixture is filtered (solid is saved)
  5. customThe mixture is separated
  6. additionThe product containing fractions
  7. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-0e401b69f7f84f9d8afd22443a44682e
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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