Hydrochloric Acid → HCID 135411157, compound

HRID 1590126Notes

Reaction equation

HRID 1590126 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9]C)=O.[C:11](#[N:16])[CH2:12][CH2:13][CH2:14][CH3:15].Cl.[NH4+].[OH-]>O1CCOCC1>[CH2:12]([C:11]1[NH:16][C:7](=[O:9])[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[N:1]=1)[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8061ValeronitrileHCID 14923Ammonium HydroxideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 135411157HCID 135411157, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3.14 g (0.02 mol) of methyl 3-amino-thiophene-2-carboxylate in 30 ml of dioxane was added 1.83 g (0.022 mol) of valeronitrile. Dry HCl was added over a period of 5 hours and the reaction mixture was then heated to 70° C. for 3 hours. The mixture was allowed to stand overnight at room temperature. The reaction mixture was diluted with 200 ml of ice water, made basic by addition of NH4OH and after standing for 30 minutes was filtered, and the filtrate concentrated in vacuo. The residue was purified by flash chromatography eluting with 50% EtOAc/hexanes after applying a suspension of the product in CH2Cl2 to the column. 1H-NMR (CDCl3): 0.96 (t, 3H, J=7.4 Hz), 1.44 (m, 2H), 1.62 (bs, 1H), 1.82 (m, 2H), 2.79 (3 line m, 2H, J=7.8 Hz), 7.33 (d, 1H, J=5.3 Hz), 7.81 (d, 1H, J=5.3 Hz).

Workup

  1. waitafter standing for 30 minutes
  2. filtrationwas filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by flash chromatography
  5. washeluting with 50% EtOAc/hexanes
  6. additiona suspension of the product in CH2Cl2 to the column

Sources & evidence

ORD record
ord-465f1eff08fa494492cb76c757c94a6a
Source dataset
uspto-grants-1993_04
Patent number
US05202328

Reaction notes

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