Hydrochloric Acid → HCID 19349148, compound

HRID 1637377Notes

Reaction equation

HRID 1637377 reaction equation
Cl[C:2]1[CH:25]=[CH:24][C:5]2=[N:6][N:7]([C:9]3[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]=3[OH:23])[N:8]=[C:4]2[CH:3]=1.CN1CCCC1=O.[OH-].[K+].[CH2:35]([SH:43])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].Cl>C1(C)C(C)=CC=CC=1>[CH2:35]([S:43][C:2]1[CH:25]=[CH:24][C:5]2=[N:6][N:7]([C:9]3[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]=3[OH:23])[N:8]=[C:4]2[CH:3]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81441-OctanethiolHCID 13387N-methyl-2-pyrrolidoneHCID 14797Potassium HydroxideHCID 774702,4-Di-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)phenol

Product 1

HCID 19349148HCID 19349148, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
172.5 °C

Procedure

To a 500-mL, round-bottomed flask are charged 30 g (0.083 mol) of 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole, 65 g (0.65 mol) of N-methyl-pyrrolidinone, 13.5 g (0.21 mol) of potassium hydroxide pellets and 25 g (0.16 mol) of n-octyl mercaptan are added. The mixture is agitated and the resultant slurry is heated to 170-175° C. and held at that temperature for 4.5 hours. The reaction mixture is then cooled to 120° C. at which time 150 g of xylene and 90 g of 10% aqueous hydrochloric acid are added. The brine layer is split off and the xylene phase at 90° C. is washed three times with water. Xylene is partially distilled under vacuum and then 80 g of methanol are added. The temperature of the reaction mixture is reduced to ambient temperature to induce crystallization. The yellow slurry formed is further cooled to 0-5° C. and filtered. The wetcake is washed with 100 g of cold methanol and dried to constant weight. The title compound is obtained as yellow needles in a yield of 37.7 g (97%). The structure of the product is verified by 1HNMR and mass spectroscopy.

Workup

  1. additionare added
  2. additionare added
  3. customThe brine layer is split off
  4. washthe xylene phase at 90° C. is washed three times with water
  5. distillationXylene is partially distilled under vacuum
  6. addition80 g of methanol are added
  7. customis reduced to ambient temperature
  8. customcrystallization
  9. customThe yellow slurry formed
  10. temperatureis further cooled to 0-5° C.
  11. filtrationfiltered
  12. washThe wetcake is washed with 100 g of cold methanol
  13. customdried to constant weight

Sources & evidence

ORD record
ord-807b9b09d2cb4dc5b51b5230df44b753
Source dataset
uspto-grants-2000_03
Patent number
US06040455

Reaction notes

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