Water → HCID 86614627, compound

HRID 883982Notes

Reaction equation

HRID 883982 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:21]=[C:20]([Cl:22])[N:19]=[C:18]([NH2:23])[N:17]=2)=[C:11]([N+:24]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].O1CCCC1.O>CO.[Fe]>[NH2:24][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=[CH:13][C:12]=1[S:15][C:16]1[CH:21]=[C:20]([Cl:22])[N:19]=[C:18]([NH2:23])[N:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86614628HCID 86614628, compound

Product 1

HCID 86614627HCID 86614627, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent2×

Procedure

A solution of the product from Example 82C (0.1 g, 0.257 mmol), iron powder (0.058 g, 1.03 mmol) and ammonium chloride (0.017 g, 0.310 mmol) in a methanol (5 mL), tetrahydrofuran (5 mL), and water (2 mL) solution was heated to reflux for 1.5 hours. The resultant mixture was diluted with methanol (50 mL) and filtered through a pad of celite. The filtrate was concentrated under vacuum to a volume of 10 mL, the solution diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts were washed with 10% sodium chloride then dried over magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (0.04 g, 43%).

Workup

  1. temperatureto reflux for 1.5 hours
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated under vacuum to a volume of 10 mL
  4. additionthe solution diluted with water (50 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. washThe combined extracts were washed with 10% sodium chloride
  7. dry with materialthen dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-547040738cfb485b858b68448a78564d
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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