Ethanol → HCID 20348542, compound

HRID 1701140Notes

Reaction equation

HRID 1701140 reaction equation
[CH2:1]1N2CN3CN(C2)CN1C3.BrC[C:13]1[CH:18]=[CH:17][C:16]([S:19]C(F)F)=CC=1.BrC(Br)C1C=CC(S[CH:32]([F:34])[F:33])=CC=1.[CH2:36](O)[CH3:37]>O>[F:33][CH:32]([F:34])[C:37]1[CH:36]=[CH:1][C:17]([CH:16]=[S:19])=[CH:18][CH:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 4101HexamethylenetetramineHCID 14033110HCID 14033110, compound2×HCID 20348556HCID 20348556, compound

Product 1

HCID 20348542HCID 20348542, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of hexamethylenetetramine (31.2 g; 0.22 mole) in ethanol (90 ml) and water (60 ml) under a nitrogen atmosphere a mixture of α-bromo-p-difluoromethylthiotoluene and α,α-dibromo-p-difluoromethylthiotoluene (31.3 g; 27:73 mixture of Example 8) is added. The reaction mixture is heated at reflux for 2 hours then stirred at room temperature for 16 hours. It is then diluted with water (500 ml) and extracted 3X with ether. The ether layer is washed with water, saturated salt solution and dried over magnesium sulfate. The ethereal solution is concentrated to afford 15.0 g (80%) of the title product, a yellow oil; 90% real by NMR.

Workup

  1. additionis added
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 2 hours
  4. extractionextracted 3X with ether
  5. washThe ether layer is washed with water, saturated salt solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe ethereal solution is concentrated

Sources & evidence

ORD record
ord-0d366e78de3f496eb497e05cb7d359dc
Source dataset
uspto-grants-1980_03
Patent number
US04191768

Reaction notes

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