Hexane → HCID 14349415, compound

HRID 2231842Notes

Reaction equation

HRID 2231842 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])#[N:2].[Cl:14][C:15]([Cl:19])([Cl:18])[S:16]Cl.C(N(CC)CC)C.CCCCCC>C(Cl)Cl>[C:1]([CH2:3][N:4]([S:16][C:15]([Cl:19])([Cl:18])[Cl:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])#[N:2]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 11666Trichloromethanesulfenyl chlorideHCID 3288130HCID 3288130, compound

Product 1

HCID 14349415HCID 14349415, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 5.0 g (0.026 mole) N-Cyanomethyl-2-chlorobenzamide (the product of Example 8) and 5.3 g (0.029 mole) trichloromethylsulfenyl chloride in 125 ml methylene chloride, 3.2 g (0.032 mole) triethylamine in 25 ml methylene chloride were dropped in over 35 minutes. The reaction mixture was stirred about 25 minutes. The reaction mixture was washed three times with 75 ml water, dried over magnesium sulfate and stripped to give a brown oil. Hexane (25 ml) was added to the oil which crystallized when cooled in an ice bath.

Workup

  1. additionwere dropped in over 35 minutes
  2. washThe reaction mixture was washed three times with 75 ml water
  3. dry with materialdried over magnesium sulfate
  4. customto give a brown oil
  5. customcrystallized when
  6. temperaturecooled in an ice bath

Sources & evidence

ORD record
ord-6113bfe8201247d4804f49f811db7544
Source dataset
uspto-grants-1988_11
Patent number
US04785019

Reaction notes

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