Triethylamine → HCID 21284990, compound

HRID 2231846Notes

Reaction equation

HRID 2231846 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)=[O:6])#[N:2].[Cl:17][C:18]([Cl:24])([S:22]Cl)[CH:19]([Cl:21])[Cl:20].C(N(CC)CC)C>C(Cl)Cl>[C:1]([CH2:3][N:4]([S:22][C:18]([Cl:24])([Cl:17])[CH:19]([Cl:21])[Cl:20])[C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 14349402HCID 14349402, compound

Product 1

HCID 21284990HCID 21284990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 5.0 g (0.024 N-cyanomethyl-1-naphthamide (the product of Example 11) and 6.2 g (0.026 mole) 1,1,2,2-tetrachloroethylsulfenyl chloride in 125 ml methylene chloride, 3.0 g (0.030 mole) triethylamine in 25 ml methylene chloride were dropped in over 40 minutes. The reaction mixture was stirred 30 minutes. The reaction mixture was washed three times with 75 ml portions of water, dried over magnesium sulfate, and stripped down to a volume of 50 ml. The methylene chloride solution was then chromatographed on a column containing about 125 g silica gel, eluting with methylene chloride. The eluate was stripped to give 4.3 g of the above-identified product as an amber glass which tended to crystallize slowly.

Workup

  1. additionwere dropped in over 40 minutes
  2. washThe reaction mixture was washed three times with 75 ml portions of water
  3. dry with materialdried over magnesium sulfate
  4. customThe methylene chloride solution was then chromatographed on a column
  5. additioncontaining about 125 g silica gel
  6. washeluting with methylene chloride

Sources & evidence

ORD record
ord-06b8c274854549b0b7b13800e2d7d086
Source dataset
uspto-grants-1988_11
Patent number
US04785019

Reaction notes

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