Hydrochloric Acid → HCID 21183914, compound

HRID 1384927Notes

Reaction equation

HRID 1384927 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[S:11][N:10]=[N:9][C:8]=1[C:12]([O:14]CC)=[O:13])=[O:5])[CH3:2].Cl>C(O)C>[CH2:1]([O:3][C:4]([NH:6][C:7]1[S:11][N:10]=[N:9][C:8]=1[C:12]([OH:14])=[O:13])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21184064HCID 21184064, compound

Product 1

HCID 21183914HCID 21183914, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of sodium thiocyanate (24.30 g, 0.30 mole) in acetonitrile (120 ml), maintained at 19° C., was treated dropwise over 22 minutes with a solution of ethyl chloroformate (28.7 ml, 0.30 mole) in acetonitrile (25 ml). The resultant mixture was stirred for 25 minutes at 20° C. and then ethyl diazoacetate (31.5 ml, 0.30 mole) was added. After stirring for 24 hours, 6.0 N hydrochloric acid (300 ml) was added with cooling Acetonitrile solvent was removed in vacuo and the residual aqueous suspension was extracted several times with ether. Combined ether extracts were washed with water, dried (Na2SO4) and evaporated to leave 51.0 g of ethyl 5-ethoxycarbonylamino-1,2,3-thiadiazole-4-carboxylate. This ester was hydrolyzed by refluxing for 6 hours in a mixture of ethanol (80 ml) and aqueous 6 N hydrochloric acid (400 ml) to yield the title acid; m.p. 179°-180° dec. after crystallization from nitromethane.

Workup

  1. customto yield the title acid
  2. customm.p. 179°-180° dec. after crystallization from nitromethane

Sources & evidence

ORD record
ord-d6c6fc26e505419ba80f0570b4ef10f2
Source dataset
uspto-grants-2001_07
Patent number
US06262059B1

Reaction notes

Loading…