Hydrochloric Acid → HCID 178517399, compound

HRID 131201

Reaction equation

HRID 131201 reaction equation
Cl.[NH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([O:10]C)=O.[CH:12]1([C:15]#[N:16])[CH2:14][CH2:13]1.[NH4+].[OH-]>O1CCOCC1.O>[CH:12]1([C:15]2[N:16]=[C:8]([OH:10])[C:4]3[S:5][CH:6]=[CH:7][C:3]=3[N:2]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 79637CyclopropanecarbonitrileHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 178517399HCID 178517399, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Dry HCl gas was bubbled through a solution of methyl 3-aminothiophene-2-carboxylate (1.64 g, 10.4 mmol) and cyclopropanecarbonitrile (27 mL) in dioxane (40 mL) for 1 h then the reaction mixture was diluted with cold water (2 volumes), basified with NH4OH (50 mL) and the resulting solid filtered and air dried to give the title compound (1.44 g, 72%) as a white solid: IR νmax (Nujol)/cm−1 2925, 1664, 1597, 788; NMR δH (400 MHz, DMSO) 1.04 (4H, m), 2.00 (1H, m), 7.20 (1H, d J 5.0 Hz), 8.10 (1H, d, J 5.0 Hz) and 12.60 (1H,br).

Workup

  1. filtrationthe resulting solid filtered
  2. customair dried

Sources & evidence

ORD record
ord-ec448f144c3441c5b13a1991b7d268fa
Source dataset
uspto-grants-2008_06
Patent number
US07384949B2

Linked notes

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