Ammonia → HCID 21318015, compound

HRID 263044Notes

Reaction equation

HRID 263044 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[CH:10][C:11]([N+:15]([O-])=O)=[C:12]([NH2:14])[CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].N.O>C(O)C.CCOCC>[C:1]1([S:7][C:8]2[CH:9]=[CH:10][C:11]([NH2:15])=[C:12]([NH2:14])[CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 24489Sodium Dithionite2×HCID 21318009HCID 21318009, compound

Product 1

HCID 21318015HCID 21318015, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 3.5 g (0.014 mole) of 5-(1-cyclohexen-1-ylthio)-2-nitrobenzene-amine in 125 ml of absolute ethanol under N2 there is added a solution of 8.4 g of Na2S2O4, 8.4 ml of concentrated aqueous ammonia and 52.5 ml of water. The mixture is refluxed for 15 minutes and an additional 0.8 g of Na2S2O4 is added. After an additional 15 minutes reflux period TLC (silica, Et2O) shows no starting material present. The ethanol is removed in vacuo; the aqueous residue is taken to pH 12 with 50% aqueous NaOH and then extracted with CH2Cl2. The organic extracts are combined, dried (MgSO4) and evaporated to give an oil which is used immediately in the following reaction.

Workup

  1. temperatureThe mixture is refluxed for 15 minutes
  2. customThe ethanol is removed in vacuo
  3. extractionextracted with CH2Cl2
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give an oil which
  7. customis used immediately in the following reaction

Sources & evidence

ORD record
ord-c6f521843b5349c49816ba87e06ca9c5
Source dataset
uspto-grants-1979_05
Patent number
US04156006

Reaction notes

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