Methanol → HCID 18796983, compound

HRID 1003400Notes

Reaction equation

HRID 1003400 reaction equation
[Na].[NH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9](Cl)[CH:10]=2)[S:5][C:4]=1[C:13]([O:15][CH3:16])=[O:14].[CH3:17][OH:18]>>[NH2:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[C:9]([O:18][CH3:17])[CH:10]=2)[S:5][C:4]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545Sodium2×HCID 18796854HCID 18796854, compound

Product 1

HCID 18796983HCID 18796983, compoundYield 86%

Procedure

Sodium metal (0.46 g, 20 mmol) was added to methanol (20 mL) and allowed to react until metallic sodium was consumed. To the solution was added the product from Example 32A (0.485 g, 2.0 mmol) and the reaction was heated to reflux for 2 h. The reaction was quenched in sat. aq. NH4Cl and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated to yield 0.410 g (86%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 3.88(s, 3H), 4.02 (s, 3H), 6.74 (d, 1H), 7.77 (d, 1H).

Workup

  1. customwas consumed
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 2 h
  4. customThe reaction was quenched in sat. aq. NH4Cl
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-47b01ecf0ca5494d8aeddc3908470c2c
Source dataset
uspto-grants-2000_04
Patent number
US06046207

Reaction notes

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