Methanol → HCID 21466888, compound

HRID 1939125Notes

Reaction equation

HRID 1939125 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

13.2 g of glycylglycine, 200 ml of methanol, 20 g of triethylamine, and 15 g of carbon disulfide were placed in a flask having a capacity of 500 ml, and stirred at 30° C. for 1 hour. 12.3 g of ethyl chloroacetate dissolved in 50 ml of methanol was dropwise added thereto, then stirred at room temperature for 30 minutes. The obtained solution was yellowish orange. After the solvent was distilled off under reduced pressure, 50 ml of ethanol was added, and 15 g of potassium acetate dissolved in 300 ml of ethanol was further added thereto. The precipitated crystals were recovered by filtration, washed with ethanol to thereby obtain 15.4 g of rhodanine-3-ylmethylcarbamoylacetic acid.

Workup

  1. additionwas dropwise added
  2. stirringstirred at room temperature for 30 minutes
  3. distillationAfter the solvent was distilled off under reduced pressure, 50 ml of ethanol
  4. additionwas added
  5. dissolution15 g of potassium acetate dissolved in 300 ml of ethanol
  6. additionwas further added
  7. filtrationThe precipitated crystals were recovered by filtration
  8. washwashed with ethanol

Sources & evidence

ORD record
ord-0791505a9715418898adf6728b1415bb
Source dataset
uspto-grants-1997_12
Patent number
US05695909

Reaction notes

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