Sodium Hydroxide → HCID 13015383, compound

HRID 1863356Notes

Reaction equation

HRID 1863356 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:22](C)([CH3:27])[C:23](OC)=O)[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[CH:22]([C:11]1[S:12][C:13]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]=1)([CH3:27])[CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13015382HCID 13015382, compound

Product 1

HCID 13015383HCID 13015383, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4,5-bis(p-methoxyphenyl)-α,α-dimethyl-2-thiazoleacetic acid, methyl ester (0.70 g.; 0.0018 mole), 6 N sodium hydroxide (1.6 ml.) and methanol (15 ml.) was stirred at ambient temperature for 16 hours. Methanol was removed by rotary evaporation; the residue was slurried in water (30 ml.) and then adjusted to pH 2 with conc. hydrochloric acid. Decarboxylation occurred while the mixture stirred at ambient temperature for 1.75 hours. The mixture was extracted with methylene chloride. The extracts were dried (sodium sulfate) and concentrated by rotary evaporation to afford 0.59 g. of oily product. The material crystallized slowly at -10° over a period of several days. Recrystallization from pentane afforded 0.19 g. (32% yield) of 2-isopropyl-4,5-bis(p-methoxyphenyl)thiazole; m.p. 61°-65° C.

Workup

  1. customMethanol was removed by rotary evaporation
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialThe extracts were dried (sodium sulfate)
  4. concentrationconcentrated by rotary evaporation
  5. customto afford 0.59 g
  6. customThe material crystallized slowly at -10° over a period of several days
  7. customRecrystallization from pentane
  8. customafforded 0.19 g

Sources & evidence

ORD record
ord-6d8f27e2811e47b59f46c439ebc2ecd5
Source dataset
uspto-grants-1979_09
Patent number
US04168315

Reaction notes

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