Hydrochloric Acid → HCID 20140932, compound

HRID 1252275Notes

Reaction equation

HRID 1252275 reaction equation
Cl.[CH3:2][S:3][C:4]([CH3:9])([CH3:8])[C:5]([NH2:7])=[O:6].[C:10](Cl)(Cl)=[O:11].[N:14]1[CH:19]=CC=[CH:16][CH:15]=1.[C:20]1(C)C=CC=CC=1>C(COC)OC>[CH3:8][C:4]([C:5]1[O:6][C:10](=[O:11])[N:14]([CH:15]([CH3:20])[CH3:16])[CH2:19][N:7]=1)([S:3][CH3:2])[CH3:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049Pyridine2×HCID 1140TolueneHCID 6371PhosgeneHCID 21150551HCID 21150551, compound

Product 1

HCID 20140932HCID 20140932, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

5 g of gaseous hydrogen chloride are introduced at -30° C. into 300 ml of dimethoxyethane, followed by the addition of 6.4 g of 1,3,5-triisopropyl-2,4,6-hexahydrotriazine. The reaction mixture is kept at -20° C., during which time 12 g of α-methylmercaptoisobutyric acid amide are added. The reaction mixture is stirred for 21/2 hours at room temperature. Then, likewise at -20° C., 50 ml of a 20% phosgene solution in toluene and, subsequently, a solution of 15 ml of pyridine in 30 ml of dimethoxyethane are added dropwise to the reaction mixture. The mixture is then stirred for 1 hour at room temperature. A further 30 ml of pyridine are then added dropwise, and the mixture is stirred for a further 4 hours at 60° C. For working up, the reaction mixture is cooled and filtered, and the filtrate is concentrated by evaporation. The residue is taken up in ethyl acetate, and the resultant solution is extracted twice with water and twice with a saturated sodium chloride solution. The separated organic phase is dried over sodium sulfate and concentrated by evaporation. The residue is taken up in hexane, a small amount of silica gel is added, and the batch is filtered. The filtrate is concentrated by evaporation, thus affording the title compound of the formula ##STR6## with a refractive index nD20 of 1.5028 (compound 1).

Workup

  1. additionare added
  2. stirringThe mixture is then stirred for 1 hour at room temperature
  3. stirringthe mixture is stirred for a further 4 hours at 60° C
  4. temperaturethe reaction mixture is cooled
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated by evaporation
  7. extractionthe resultant solution is extracted twice with water and twice with a saturated sodium chloride solution
  8. dry with materialThe separated organic phase is dried over sodium sulfate
  9. concentrationconcentrated by evaporation
  10. additiona small amount of silica gel is added
  11. filtrationthe batch is filtered
  12. concentrationThe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-965bfdd760aa4326825ac1aae6c9aee9
Source dataset
uspto-grants-1988_05
Patent number
US04742056

Reaction notes

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