Triethylamine → HCID 14349411, compound

HRID 2231843Notes

Reaction equation

HRID 2231843 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C:7]1[C:8]([CH3:13])=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:6])#[N:2].[Cl:14][C:15]([Cl:19])([Cl:18])[S:16]Cl.C(N(CC)CC)C>C(Cl)Cl>[C:1]([CH2:3][N:4]([S:16][C:15]([Cl:19])([Cl:18])[Cl:14])[C:5]([C:7]1[C:8]([CH3:13])=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11666Trichloromethanesulfenyl chlorideHCID 3425613HCID 3425613, compound

Product 1

HCID 14349411HCID 14349411, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 5.0 g (0.029 mole) N-cyanomethyl-o-toluamide (the product of Example 10) and 5.8 g (0.031 mole) trichloromethylsulfenyl chloride in 125 ml methylene chloride, 3.6 g (0.036 mole) triethylamine in 25 ml methylene chloride were added dropwise over 40 minutes. The reaction mixture was stirred 30 minutes. The reaction mixture was washed three times with 75 ml water, dried over magnesium sulfate and stripped to give a brown oil. The oil did not crystallize when rubbed with hexane. The oil was column chromatographed through 125 g of silica gel, eluting with chloroform to give 5.6 g of a glass-like product which crystallized partly upon cooling to room temperature.

Workup

  1. additionwere added dropwise over 40 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. customThe oil did not crystallize when
  6. customchromatographed through 125 g of silica gel
  7. washeluting with chloroform

Sources & evidence

ORD record
ord-befbca5628ec4293909a494d3b5a8ce0
Source dataset
uspto-grants-1988_11
Patent number
US04785019

Reaction notes

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