HCID 12653320, compound → HCID 69689226, compound

HRID 1265605Notes

Reaction equation

HRID 1265605 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([NH:19][NH2:20])=[S:18])[CH:12]=1.Cl.C([O:25][C:26](=N)[CH2:27][CH2:28]O)C>N1C=CC=CC=1.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[S:18][C:28]([CH2:27][CH2:26][OH:25])=[N:20][N:19]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 12653320HCID 12653320, compoundHCID 86586796HCID 86586796, compound

Product 1

HCID 69689226HCID 69689226, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-hydrazinothiocarbonyl-benzoic acid methyl ester trifluoroacetate (0.45 g) and 3-hydroxy-propionimidic acid ethyl ester hydrochloride (0.35 g) in pyridine (5 mL) was heated to 100° C. for 1.5 h. The mixture was diluted with AcOEt and washed with IN HCl and with brine. The organic layer was dried and evaporated and the residual oil was chromatography on silica gel using AcOEt/hexane (1:1) as eluent to give 3-[5-(2-hydroxy-ethyl)-[1,3,4]thiadiazol-2-yl]-benzoic acid methyl ester (0.37 g) as a white solid, MS (ISP) 265.3 [(M+H)+].

Workup

  1. washwashed with IN HCl and with brine
  2. customThe organic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-a8d90c3f316742968c6a85132732c142
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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