Sodium Hydroxide → HCID 19045461, compound

HRID 1591174Notes

Reaction equation

HRID 1591174 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]2[S:8][C:9]3([S:23][C:6]=2[CH:5]=1)[CH2:14][CH2:13][N:12](C(=O)C1C=CC=CC=1)[CH2:11][CH2:10]3)([O-:3])=[O:2].[OH-].[Na+]>C(O)C.O>[N+:1]([C:4]1[CH:25]=[CH:24][C:7]2[S:8][C:9]3([S:23][C:6]=2[CH:5]=1)[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19045519HCID 19045519, compound

Product 1

HCID 19045461HCID 19045461, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

1.20 grams of the nitro dithioacetal from Step B in 46 mL of ethanol was treated with 18 mL of 40% aqueous NaOH and heated to 70° C. for 8 hours. The solution was diluted with water and extracted with CH2Cl2. The organics were combined, washed with water, saturated aqueous sodium carbonate, brine, dried (Na2SO4) and concentrated to an oil. The oil was filtered through silica gel eluting with 10% CH3OH in CH2Cl2 to give the product as a yellow solid.

Workup

  1. extractionextracted with CH2Cl2
  2. washwashed with water, saturated aqueous sodium carbonate, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to an oil
  5. filtrationThe oil was filtered through silica gel eluting with 10% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-af5bff59feef4cf2b4bb5bcbcc8fa252
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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