1,2-Dichlorobenzene → Ethyl 5-phenyl-1,2,4-thiadiazole-3-carboxylate

HRID 625105Notes

Reaction equation

HRID 625105 reaction equation
O=C1[S:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])O1.[C:12](#[N:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.ClC1C=CC=CC=1Cl>>[C:13]1([C:12]2[S:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:19]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 7505BenzonitrileHCID 12351252ethyl 2-oxo-2H-1,3,4-oxathiazole-5-carboxylate

Product 1

HCID 12351254Ethyl 5-phenyl-1,2,4-thiadiazole-3-carboxylateYield 3%

Procedure

A mixture of ethyl 2-oxo-1,3,4-oxathiazole-5-carboxylate (U.S. Publication No. 2005/0096362) (1.5 g, 8.56 mmol) and benzonitrile (4.37 ml, 42.8 mmol) in 1,2-dichlorobenzene (15.42 ml, 137 mmol) was heated to 160° C. for 4 days. The reaction was then cooled down to RT and the solvent was evaporated by heated the reaction at 75° C. at maximum vacuum. The residue was purified on silica gel chromatography (100% CH2Cl2 to 3% EtOAc in CH2Cl2) to provide the title material (0.064 g, 3%). LC (Method B): 2.021 min. HRMS (ESI) calcd for C11H11N2O2S [M+H]+ m/z 235.0541, found 235. 1H NMR (CDCl3, 400 MHz) δ ppm: 8.01-8.09 (m, 1H), 7.49-7.59 (m, 2H), 4.56 (q, J=7.17 Hz, 1H), 1.50 (t, J=7.24 Hz, 1H).

Workup

  1. customthe solvent was evaporated
  2. temperatureby heated
  3. customthe reaction at 75° C. at maximum vacuum
  4. customThe residue was purified on silica gel chromatography (100% CH2Cl2 to 3% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-1632376b45314c1a8d7ca4fd2cc83cd1
Source dataset
uspto-grants-2016_04
Patent number
US09303065B2

Reaction notes

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