Acetic Acid → HCID 13173178, compound

HRID 980356Notes

Reaction equation

HRID 980356 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[CH:24]=[O:25])[CH2:21][CH2:20][S:19]3)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C.O>C(O)C>[C:12]([C:9]1[CH:8]=[C:7]([C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[CH2:24][OH:25])[CH2:21][CH2:20][S:19]3)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 13173177HCID 13173177, compound

Product 1

HCID 13173178HCID 13173178, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 10 ml of ethanol was dissolved 0.4 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-formyl-2,3-dihydroimidazo[2,1-b]thiazole and after adding 40 mg of sodium borohydride to the solution, the mixture was stirred for 10 minutes. To the reaction mixture were added 0.3 ml of acetic acid and 30 ml of water, and the crystals thus precipitated were recovered by filtration and recrystallized from aqueous ethanol to provide 0.3 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-hydroxymethyl-2,3-dihydroimidazo[2,1-b]thiazole.

Workup

  1. customthe crystals thus precipitated
  2. filtrationwere recovered by filtration
  3. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-6d03713f7bd44ced8f921990eeca1880
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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