Hydrochloric Acid → HCID 13069134, compound

HRID 2085988Notes

Reaction equation

HRID 2085988 reaction equation
C[O:2][C:3](=[O:37])/[C:4](=[N:16]\[O:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)/[C:5]1[N:9]=[C:8]([NH:10]C(OCC)=O)[S:7][N:6]=1.[OH-].[Na+].C(O)C.Cl>>[NH2:10][C:8]1[S:7][N:6]=[C:5](/[C:4](=[N:16]/[O:17][C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)/[C:3]([OH:37])=[O:2])[N:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 22726941Methyl (αZ)-5-[(ethoxycarbonyl)amino]-α-[(triphenylmethoxy)imino]-1,2,4-thiadiazole-3-acetateHCID 23692425Sodium hydroxide ethanol

Product 1

HCID 13069134HCID 13069134, compoundYield 89.7%

Conditions

Temperature
5 °C

Procedure

Into a 500 mL round bottom flask equipped with mechanical stirrer, reflux condenser and nitrogen purge was charged (Z)-methyl-2-(5-ethoxycarbonylamino-1,2,4-thiadiazol-3-yl)-triphenylmethyloxyiminoacetate (20.0 g, 0.04 mol, 1.0 eq) followed by 200 mL of a 2:1 solution of 2.5 M NaOH/ethanol. The resulting biphasic solution was heated to reflux and maintained there for 15 hours. The solution was cooled to 5° C. and the pH was slowly adjusted to 3-3.5 with concentrated HCl. The precipitated white solid was filtered and washed with cold water (3×100 mL). Removal of water by coevaporation with toluene (3×200 mL), followed by drying under high vacuum at 40° C. gave 15.44 grams of the title compound as a white fluffy solid. 1H NMR (DMSO) δ 7.20-7.45. Mass spectral analysis confirms product identity.

Workup

  1. customInto a 500 mL round bottom flask equipped with mechanical stirrer
  2. temperaturereflux condenser
  3. customnitrogen purge
  4. temperatureThe resulting biphasic solution was heated
  5. temperatureto reflux
  6. temperaturemaintained there for 15 hours
  7. filtrationThe precipitated white solid was filtered
  8. washwashed with cold water (3×100 mL)
  9. customRemoval of water by coevaporation with toluene (3×200 mL)
  10. customby drying under high vacuum at 40° C.

Sources & evidence

ORD record
ord-cd68c21f5d35433e92a4ae84966a7bc2
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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