Hydrochloric Acid → HCID 21183914, compound

HRID 866758Notes

Reaction equation

HRID 866758 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-0ce0b7d5e65245a39bf6010d45ce23d4
Source dataset
uspto-grants-1978_07
Patent number
US04101548

Reaction notes

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