Benzene → HCID 13107035, compound

HRID 980343Notes

Reaction equation

HRID 980343 reaction equation
C1C=CC=CC=1.[C:7]([C:11]1[CH:12]=[C:13]([C:22]2[N:23]=[C:24]([SH:27])[S:25][CH:26]=2)[CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])([CH3:10])([CH3:9])[CH3:8].Br[CH2:29][C:30]([OH:32])=[O:31]>C(N(CC)CC)C>[C:7]([C:11]1[CH:12]=[C:13]([C:22]2[N:23]=[C:24]([S:27][CH2:29][C:30]([OH:32])=[O:31])[S:25][CH:26]=2)[CH:14]=[C:15]([C:18]([CH3:20])([CH3:21])[CH3:19])[C:16]=1[OH:17])([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 241BenzeneHCID 6227Bromoacetic AcidHCID 178440667HCID 178440667, compound

Product 1

HCID 13107035HCID 13107035, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 20 ml of benzene were added 0.64 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-mercaptothiazole and 0.32 g of bromoacetic acid and then 0.5 g of triethylamine was added dropwise to the mixture with stirring. After one hour, triethylamine hydrobromide thus precipitated was filtered off and the benzene solution was extracted with 10 ml of a 2% sodium hydroxide solution. The aqueous extract was acidified by the addition of hydrochloric acid and extracted with ether. The ether solution was dried over anhydrous sodium sulfate and concentrated. The crystals thus obtained were recrystallized from benzene to provide 0.52 g of [4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-thiazolylthio]acetic acid.

Workup

  1. customtriethylamine hydrobromide thus precipitated
  2. filtrationwas filtered off
  3. extractionthe benzene solution was extracted with 10 ml of a 2% sodium hydroxide solution
  4. extractionThe aqueous extract
  5. additionwas acidified by the addition of hydrochloric acid
  6. extractionextracted with ether
  7. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe crystals thus obtained
  10. customwere recrystallized from benzene

Sources & evidence

ORD record
ord-b758da1991bc44b3ad9fe9d4d2e91c07
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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