Methanol → HCID 21466888, compound

HRID 1377939Notes

Reaction equation

HRID 1377939 reaction equation
N[CH2:2][C:3]([NH:5][CH2:6]C(O)=O)=[O:4].[CH2:10]([N:12](CC)CC)[CH3:11].[C:17](=[S:19])=[S:18].ClC[C:22]([O:24]CC)=[O:23].C[OH:28]>>[S:18]1[CH2:11][C:10](=[O:28])[N:12]([CH2:6][NH:5][C:3]([CH2:2][C:22]([OH:24])=[O:23])=[O:4])[C:17]1=[S:19]

Participants

6

Reactant 5

HCID 887Methanol2×HCID 6348Carbon DisulfideHCID 7751Ethyl chloroacetateHCID 8471TriethylamineHCID 11163Glycylglycine

Product 1

HCID 21466888HCID 21466888, compound

Conditions

Temperature
30 °C

Procedure

Into a 500-ml flask were placed 13.2 g of glycylglycine, 200 ml of methanol, 20 g of triethylamine, and 15 g of carbon disulfide. The contents were stirred at 30° C. for 1 hour. A solution of 12.3 g of ethyl chloroacetate in 50 ml of methanol was added thereto dropwise, and this mixture was stirred at room temperature for 30 minutes. The resulting solution assumed a yellowish orange color. After the solvent was distilled off under reduced pressure, 50 ml of ethanol was added to the residue, and a solution of 15 g of potassium acetate in 300 ml of ethanol was added thereto. The crystals precipitated were taken out by filtration and washed with ethanol to obtain 15.4 g of rhodanin-3-ylmethylcarbamoylacetic acid.

Workup

  1. customInto a 500-ml flask were placed
  2. stirringdropwise, and this mixture was stirred at room temperature for 30 minutes
  3. distillationAfter the solvent was distilled off under reduced pressure, 50 ml of ethanol
  4. additionwas added to the residue
  5. additiona solution of 15 g of potassium acetate in 300 ml of ethanol was added
  6. customThe crystals precipitated
  7. filtrationwere taken out by filtration
  8. washwashed with ethanol

Sources & evidence

ORD record
ord-f6ce621ba46c4da7b62f799bebf71245
Source dataset
uspto-grants-1997_09
Patent number
US05665887

Reaction notes

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