Cysteamine → 2-Nitromethylene-thiazolidine

HRID 1259415Notes

Reaction equation

HRID 1259415 reaction equation
[CH3:1][S:2][C:3](SC)=[CH:4][N+:5]([O-:7])=[O:6].[NH2:10][CH2:11]CS.C(OC(=O)C)C>C(O)C.CCCCCC>[N+:5]([CH:4]=[C:3]1[NH:10][CH2:11][CH2:1][S:2]1)([O-:7])=[O:6]

Participants

6

Reactant 3

HCID 6058CysteamineHCID 8857Ethyl AcetateHCID 836231,1-Bis(methylthio)-2-nitroethylene

Product 1

HCID 38355832-Nitromethylene-thiazolidineYield 46.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

TEA (1.8 mL, 13.20 mmol) was added to a solution of 1,1-bis-methylsulfanyl-2-nitro-ethene (I-1b: 1.45 g, 8.802 mmol) and 2-amino-ethanethiol (1 g, 8.802 mmol) in ethanol (20 mL). The resulting mixture was heated to reflux for 3 hours. The reaction mixture was monitored by TLC (70% ethylacetate in hexane). The reaction mixture was concentrated to afford the crude product. Purification by column chromatography on silica gel (70% ethylacetate in hexane) afforded 0.6 g of the product (31% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated
  4. customto afford the crude product
  5. customPurification by column chromatography on silica gel (70% ethylacetate in hexane)

Sources & evidence

ORD record
ord-31fa5a8c7fe04ab397f2affcfb352144
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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