Chloroform → HCID 13335411, compound

HRID 235677Notes

Reaction equation

HRID 235677 reaction equation
C(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#[N:14])=[CH:8][CH:7]=1.C1(S([S:24][CH2:25][CH:26]([N:38]([CH3:40])[CH3:39])[CH2:27][S:28]S(C2C=CC=CC=2)(=O)=O)(=O)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[C:13]([C:12]1([C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=2)[S:28][CH2:27][CH:26]([N:38]([CH3:40])[CH3:39])[CH2:25][S:24]1)#[N:14]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 87176BensultapHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 13335411HCID 13335411, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 20 ml of chloroform were added 1.52 g (0.01 mole) of p-chlorophenylacetonitrile and 4.3 g (0.01 mole) of 1,3-bis(benzenesulfonylthio)-2-(N,N-dimethylamino)propane, and then 3.1 g (0.02 mole) of 1,8-diazabicyclo[5,4,0]undeca-7-ene was added thereto at room temperature. After completion of addition, the reaction was allowed to proceed at 40° C. for 4 hours. The reaction mixture was washed with two 20-ml portions of water, dried over anhydrous magnesium sulfate and concentrated to dryness. The crystals thus obtained were heated in 10 ml of toluene for dissolution and the solution was allowed to stand in the cold overnight. The resulting crystalline precipitate was collected by filtration to give 2.6 g (87%) of 2-cyano-2-(p-chlorophenyl)-5-(N,N-dimethylamino)-1,3-dithiane as light-yellow crystals melting at 110°-111° C.

Workup

  1. customat room temperature
  2. additionAfter completion of addition
  3. washThe reaction mixture was washed with two 20-ml portions of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crystals thus obtained
  7. customto stand in the cold overnight
  8. filtrationThe resulting crystalline precipitate was collected by filtration

Sources & evidence

ORD record
ord-8997a9f405414f94b8459f34e6239624
Source dataset
uspto-grants-1987_02
Patent number
US04640929

Reaction notes

Loading…