Ethylenediamine → HCID 86748070, compound

HRID 1742180Notes

Reaction equation

HRID 1742180 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]=1[C:12]([OH:14])=O.[C:15](C1NC=CN=1)([C:17]1[NH:18]C=CN=1)=O.C(N)C[NH2:29]>ClCCl>[NH2:18][CH2:17][CH2:15][C:8]1[C:7]2[C:3]([O:2][CH3:1])=[C:4]([C:12]([NH2:29])=[O:14])[S:5][C:6]=2[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 880203-Methoxybenzo(b)thiophene-3-carboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 86748070HCID 86748070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Methoxy benzothiophene 2-carboxylic acid (6.24 g) and carbonyl diimidazole (5.8 g) were dissolved in dry dichloromethane (200 ml) and stirred at room temperature for 2 hours. The solution was then added to a solution of ethylene diamine (9.0 g) in dichloromethane (50 ml) and the solution stirred overnight. After evaporation to dryness under vacuum, the residue was partitioned between ethyl acetate and water. The organic layer was extracted several times with 2N hydrochloric acid, the aqueous layer washed with ethyl acetate and then made basic with 0.88 ammonia solution. This was extracted with ethyl acetate (3×100 ml), washed with water, dried and evaporated to dryness under vacuum, to give 2-amino ethyl-3-methoxy benzothiophene-2-carboxamide.

Workup

  1. stirringthe solution stirred overnight
  2. customAfter evaporation to dryness under vacuum
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe organic layer was extracted several times with 2N hydrochloric acid
  5. washthe aqueous layer washed with ethyl acetate
  6. extractionThis was extracted with ethyl acetate (3×100 ml)
  7. washwashed with water
  8. customdried
  9. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-be3fd1468b1c4c909813ac1706012efe
Source dataset
uspto-grants-1994_08
Patent number
US05338735

Reaction notes

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