Triethylamine → HCID 13023070, compound

HRID 1982275Notes

Reaction equation

HRID 1982275 reaction equation
[FH:1].[CH3:2][N:3]=[C:4]=[O:5].C[CH2:7][C:8]([NH:10][S:11]Cl)=[O:9].[CH2:13](N(CC)CC)C>C1(C)C=CC=CC=1.O>[CH3:2][N:3]([S:11][N:10]([CH3:13])[C:8](=[O:9])[CH3:7])[C:4]([F:1])=[O:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 14917Hydrofluoric AcidHCID 88676034HCID 88676034, compound

Product 1

HCID 13023070HCID 13023070, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
8 °C

Procedure

To a solution of 13.32 g hydrogen fluoride in 100 ml toluene, cooled to -50° C., was added 38.05 g of methyl isocyanate. The reaction mixture was allowed to warm to approximately 8° C. and stirred at that temperature for 1.5 hr. Then 93.0 g of N-methylacetylaminosulfenyl chloride dissolved in 250 ml toluene was added followed by dropwise addition of 67.4 g of triethylamine. The temperature was maintained at 0°-5° C. during the addition. After stirring at ambient temperature for 0.5 hr, the reaction mixture was diluted with 200 ml water. The toluene extract was further washed with water, dried with magnesium sulfate and evaporated in vacuo. Distillation of the residue yielded 40.0 g of product; b.p. 70°-74° C./0.5 mm.

Workup

  1. additionwas added
  2. temperatureThe temperature was maintained at 0°-5° C. during the addition
  3. stirringAfter stirring at ambient temperature for 0.5 hr
  4. extractionThe toluene extract
  5. washwas further washed with water
  6. dry with materialdried with magnesium sulfate
  7. customevaporated in vacuo
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-bd22524bb5964611912c30eccbfca1d1
Source dataset
uspto-grants-1986_06
Patent number
US04595769

Reaction notes

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