Triethylamine → HCID 53720207, compound

HRID 1763395Notes

Reaction equation

HRID 1763395 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. Infra-red (neat) 4.53 (C≡N), 5.6 (C=O), 6.4, 6.9, 7.05, 7.3, 7.7, 8.5, 9.2, 10.4, 12.4, 13.3μ. NMR (CDCl3) δ 1.65 (s), 3H; 3.50 (s), 3H; 3.73 (d), JAB = 12.0 HZ and 3.98 (d), JBA = 12.0 HZ, 2H.

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-009697ec37e9440d8c140350717b3519
Source dataset
uspto-grants-1978_09
Patent number
US04111989

Reaction notes

Loading…