Hydrochloric Acid → 5-n-Butylthio-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotnazole

HRID 990203Notes

Reaction equation

HRID 990203 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.[CH2:26]([SH:30])[CH2:27][CH2:28][CH3:29].[OH-].[K+].CN1CCCC1=O.Cl>>[CH2:26]([S:30][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)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8012ButanethiolHCID 13387N-methyl-2-pyrrolidoneHCID 14797Potassium HydroxideHCID 774702,4-Di-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)phenol

Product 1

HCID 186728395-n-Butylthio-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotnazole

Conditions

Temperature
150 °C

Procedure

5-Chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)2H-benzotriazole (21.2 g, 0.06 mol), n-butyl mercaptan (7.2 g, 0.08 mol), potassium hydroxide (6.7.1 g, 0.12 mol) and N-methylpyrrolidone (50 g, 0.5 mol) are charged to a reactor and heated to 150° C. The reaction mass is held at 150° C. for 4.5 hours at which time it then cooled to ambient temperature. A mixture of 15 g of concentrated hydrochloric acid aand 70 g of ice are then added to the reactor. The solids are filtered off and washed with water. Thirty gram of crude, wet, yellow crystals are obtained as the title compound. This product can be used “as is” in procedure of Example 33.

Workup

  1. temperaturethen cooled to ambient temperature
  2. additionare then added to the reactor
  3. filtrationThe solids are filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-3474b9ee14db4f6a94ff41124b3e11d1
Source dataset
uspto-grants-2002_10
Patent number
US06458872B1

Reaction notes

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