Triethylamine → HCID 14349426, compound

HRID 2231840Notes

Reaction equation

HRID 2231840 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[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](=[O:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11666Trichloromethanesulfenyl chlorideHCID 231599N-(Cyanomethyl)-2-phenylethanimidic acid

Product 1

HCID 14349426HCID 14349426, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 4.9 g (0.028 mole) N-cyanomethyl phenylacetamide (the product of Example 6) and 5.7 g (0.031 mole) trichloromethylsulfenyl chloride in ml methylene chloride which had been cooled in an ice bath, 3.5 g (0.035 mole) triethylamine in 25 ml methylene chloride were dropped in over 20 minutes. The reaction mixture was washed three times with 75 ml portions of water, dried over magnesium sulfate and stripped to give 8.0 g of a dark brown oil, which failed to crystallize.

Workup

  1. temperaturehad been cooled in an ice bath
  2. washThe reaction mixture was washed three times with 75 ml portions of water
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-1b8fc82c05ef4313855fdd626a7776bf
Source dataset
uspto-grants-1988_11
Patent number
US04785019

Reaction notes

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