2-Mercaptoethanol → HCID 23298249, compound

HRID 1953457Notes

Reaction equation

HRID 1953457 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].Cl[C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8](=[O:19])[C:7]=1[N+:20]([O-:22])=[O:21].C(N(CC)CC)C>C(O)C>[CH2:17]([O:16][C:14]([CH2:13][N:9]1[C:10]([CH3:12])=[CH:11][C:6]([S:1][CH2:2][CH2:3][OH:4])=[C:7]([N+:20]([O-:22])=[O:21])[C:8]1=[O:19])=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 23298254HCID 23298254, compound

Product 1

HCID 23298249HCID 23298249, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Mercaptoethanol (0.168 mL, 2.4 mmol) was added to a stirred mixture of 4-chloro-1-ethyloxycarbonylmethyl-6-methyl-3-nitro-2-pyridinone (the product of Example 3, Step B, 549 mg, 2.0 mmol) and triethylamine (0.613 mL, 4.4 mmol) in ethanol (4 mL) and the mixture was heated to reflux for 15 min. The reaction was cooled and evaporated to a solid which was purified by flash column chromatography on silica gel (eluting with ethyl acetate), to give the title compound as a pale yellow crystalline solid:

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 15 min
  3. temperatureThe reaction was cooled
  4. customevaporated to a solid which
  5. customwas purified by flash column chromatography on silica gel (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-ce925ecd261e4b7cbbb18ff4413f6cbf
Source dataset
uspto-grants-2000_09
Patent number
US06117888

Reaction notes

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