Hydrochloric Acid → HCID 14871959, compound

HRID 1463510Notes

Reaction equation

HRID 1463510 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[S:11][C:10]([C:12]([O:14]C)=[O:13])=[CH:9][CH:8]=2)[O:4][N:3]=1.Cl>[OH-].[Na+].C(O)C>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=2)[O:4][N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14871957HCID 14871957, compound

Product 1

HCID 14871959HCID 14871959, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of methyl 5-(3-methyl-1,2,4-oxadiazol-5-yl)-2-thiophenecarboxylate, prepared according to Example 81, (1.09 g, 4.86 mmole) in 35 ml of 2N sodium hydroxide was diluted with 5 ml of ethanol and warmed to 65° C. for thirty minutes. The solution was cooled in an ice bath and acidified to pH 2 with concentrated hydrochloric acid. Filtration and drying furnished 870 mg (85% yield) of the title compound as an off-white solid. The analytical sample was recrystallized from methanol, m.p. 226°-8° C. Analysis: Calculated for C8H6N2O3S: C, 45.70; H, 2.88; N, 13.33%. Found: C, 45.57; H, 2.75; N, 13.37%. EIMS (m/z): 210 (M+, base) and 153 (M+ --C2H3NO, 99%); 1H-NMR (DMSO-d6) delta, 7.97 (1H, d, J 3.9 Hz), 7.82 (1H, d, J=3.9 Hz) and 2.40 (3H, s); ir (potassium bromide): 3112 (br), 1699, 1289, 1112 and 840 cm-1.

Workup

  1. customprepared
  2. temperatureThe solution was cooled in an ice bath
  3. filtrationFiltration
  4. customdrying

Sources & evidence

ORD record
ord-2cd7a229e3314e30b0dc6685edfc792e
Source dataset
uspto-grants-1994_04
Patent number
US05300655

Reaction notes

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