Hydrochloric Acid → 1,1-Dioxo-1,3-thiazolidine-4-carboxamide hydrochloride

HRID 624986Notes

Reaction equation

HRID 624986 reaction equation
[ClH:1].O1CCOCC1.[C:8]([CH:11]1[CH2:15][S:14](=[O:17])(=[O:16])[CH2:13][N:12]1C(OC(C)(C)C)=O)(=[O:10])[NH2:9]>ClCCl>[ClH:1].[O:16]=[S:14]1(=[O:17])[CH2:15][CH:11]([C:8]([NH2:9])=[O:10])[NH:12][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90204869tert-Butyl 4-carbamoyl-1,1-dioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 902038431,1-Dioxo-1,3-thiazolidine-4-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice cold 4 M solution of HCl in dioxane (4.73 mL, 18.9 mmol) was added to a solution of tert-butyl 4-carbamoyl-1,1-dioxo-1,3-thiazolidine-3-carboxylate (Example 127 c, 500 mg, 1.89 mmol) in dichloromethane (10.2 mL). The mixture was stirred for 4 d at ambient temperature. Removal of the solvent in vacuo yielded the title compound (388 mg, quant.) as white solid which was used in the next step without further purification, MS (ESI) m/e=198.99 [M−H−].

Workup

  1. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-ae7109127a46434989fa047a5a919d54
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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