Hydrochloric Acid → HCID 68642093, compound

HRID 1498967Notes

Reaction equation

HRID 1498967 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[N:15]1[CH2:20][CH2:19][S:18][CH2:17][C:16]1=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-])=O.O.Cl>C(O)C.[Fe]>[CH2:19]1[C:20]2[N:15]([C:14]3[C:4]([N:1]=2)=[CH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12][CH:13]=3)[CH2:16][CH2:17][S:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68642107HCID 68642107, compound

Product 1

HCID 68642093HCID 68642093, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Ethyl 3-nitro-4-(3-oxothiomorpholin-4-yl)benzoate (2.00 g, 6.44 mmol) prepared in the Step 40-1-2 was dissolved in ethanol (120 ml). Purified water (12 ml), iron powder (2.62 g, 47.04 mmol) and hydrochloric acid (0.5 ml) was added to the solution, and the mixture was heated under reflux for 4 hours. The mixture was concentrated, and a saturated sodium bicarbonate solution was added thereto, and the resulting mixture was subjected to extraction with chloroform. The extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2) to give the title compound (0.90 g, 53%) as a light-yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe mixture was concentrated
  4. additiona saturated sodium bicarbonate solution was added
  5. extractionthe resulting mixture was subjected to extraction with chloroform
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-f07ba5dcc749423096f82a05798be8e4
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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