Triethylamine → HCID 53720207, compound

HRID 1439196Notes

Reaction equation

HRID 1439196 reaction equation
[FH:1].[CH3:2][N:3]=[C:4]=[O:5].[Cl:6][CH2:7][C:8]([C:12]#[N:13])([S:10]Cl)[CH3:9].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:2][N:3]([S:10][C:8]([C:12]#[N:13])([CH3:9])[CH2:7][Cl:6])[C:4]([F:1])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 14917Hydrofluoric AcidHCID 20437441HCID 20437441, compound

Product 1

HCID 53720207HCID 53720207, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-50 °C

Procedure

To a mixture of 3.53g of anhydrous hydrogen fluoride in 150 ml of toluene cooled to -50° C. was added dropwise 10.05g of methyl isocyanate. After stirring for 1.5 hr. at 0° C, 30.0g of approximately 85 percent pure 1-chloro-2-cyano-2-propanesulfenyl chloride was added followed by dropwise addition of 17.8g of triethylamine. During the addition of base the temperature was maintained between 0° C and 10° C. After stirring for an additional 1 hr., the precipitated salt was removed by filtration and the filtrate was concentrated to yield 26.5g of a light yellow oil.

Workup

  1. additionDuring the addition of base the temperature
  2. temperaturewas maintained between 0° C and 10° C
  3. stirringAfter stirring for an additional 1 hr
  4. custom, the precipitated salt was removed by filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2a9766eab177434e87e53d79afe3b8a6
Source dataset
uspto-grants-1977_11
Patent number
US04058549

Reaction notes

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