Triethylamine → HCID 13023069, compound

HRID 1759011Notes

Reaction equation

HRID 1759011 reaction equation
[FH:1].[CH3:2][N:3]=[C:4]=[O:5].[CH3:6][N:7]([CH:10]=[O:11])[S:8]Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:2][N:3]([S:8][N:7]([CH3:6])[CH:10]=[O:11])[C:4]([F:1])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 14917Hydrofluoric AcidHCID 12819418HCID 12819418, compound

Product 1

HCID 13023069HCID 13023069, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of 9.0 g hydrogen fluoride in 100 ml toluene cooled to -50° C. was added 25.6 g methyl isocyanate. After stirring for 45 minutes and allowing the mixture to warm to -10° C., 56.4 g of N-methyl-N-formylaminosulfenyl chloride dissolved in 300 ml toluene was added. Triethylamine 45.4 g was added dropwise over a period of 0.5 hr while the temperature was maintained between 0° to 8° C. by external cooling. After stirring for 0.5 hr at ambient temperature, the reaction mixture was diluted with 200 ml ice water. The organic layer was separated, washed with water, dried and concentrated. Distillation of the residue yielded 22.4 g of product. b.p. 60°-62° C./0.2 mm.

Workup

  1. additionwas added
  2. temperaturewas maintained between 0° to 8° C. by external cooling
  3. stirringAfter stirring for 0.5 hr at ambient temperature
  4. customThe organic layer was separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-93155a4b4bc14bef96045be5277903bd
Source dataset
uspto-grants-1982_07
Patent number
US04338450

Reaction notes

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