Water → HCID 21318019, compound

HRID 263045Notes

Reaction equation

HRID 263045 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[NH2:15][C:16]1[CH:17]=[C:18]([SH:25])[CH:19]=[CH:20][C:21]=1[N+:22]([O-])=O.[OH2:26].[O:27]1CCCC1>Cl[Ti](Cl)(Cl)Cl>[C:1]1([S:25][C:18]2[CH:19]=[CH:20][C:21]([NH2:22])=[C:16]([N+:15]([O-:27])=[O:26])[CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

7

Reactant 5

HCID 962WaterHCID 7967CyclohexanoneHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 213180223-Amino-4-nitrobenzene-1-thiol

Product 1

HCID 21318019HCID 21318019, compound

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

To 500 ml of dry tetrahydrofuran under N2 there is added 5.0 g of cyclohexanone and then 5.5 ml of TiCl4. Then there is added a mixture of 11.0 ml of triethylamine and 8.5 g of 3-amino-4-nitrobenzenethiol in 105 ml of dry tetrahydrofuran and the mixture is stirred overnight at room temperature. Then there is added 300 ml of H2O and the mixture is extracted with dichloromethane. The organic layers are combined, dried (MgSO4) and evaporated in vacuo. The residue is chromatographed on silica gel. Elution with 1:1 PE-Et2O yields 2.8 g of 4-(1-cyclohexen-1-ylthio)-2-nitrobenzene-amine, m.p. 93°-95° C.

Workup

  1. additionThen there is added
  2. extractionthe mixture is extracted with dichloromethane
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue is chromatographed on silica gel
  6. washElution with 1:1 PE-Et2O

Sources & evidence

ORD record
ord-fbfbe2e83b3b448b85531860f03fa9b6
Source dataset
uspto-grants-1979_05
Patent number
US04156006

Reaction notes

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