Ethyl chloroformate → HCID 54189253, compound

HRID 496829Notes

Reaction equation

HRID 496829 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13].[OH-:17].[Na+]>O>[C:12]([NH:10][C:8](=[N:9][C:12]([O:14][CH2:15][CH3:16])=[O:17])[S:7][CH3:6])([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 54189253HCID 54189253, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

2-Methyl-2-thiopseudourea sulfate (15 g; 53.9 mmol; 1 eq) was suspended in 20 mL of water and cooled to 0-5° C. Ethyl chloroformate (29.2 g, 269 mmol; 5 eq) was added and the mixture was stirred for 5 minutes. Sodium hydroxide solution (25% w/w) was added drop-wise until the pH reached 8 (by pH paper). The white solid was collected by filtration and air dried to give 1,3-dicarboethoxy-2-methyl-2-thiopseudourea (22.2 g, 88%) as a white solid, mp 42-44° C. A small portion was dried in vacuo for analysis.

Workup

  1. filtrationThe white solid was collected by filtration and air
  2. customdried

Sources & evidence

ORD record
ord-dcbfed07e4254f5ea559ee2b65859348
Source dataset
uspto-grants-2005_09
Patent number
US06946554B2

Reaction notes

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