Sodium Hydroxide → HCID 14096963, compound

HRID 4345Notes

Reaction equation

HRID 4345 reaction equation
C([NH:4][C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[CH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:12]=1)(=O)C.[OH-].[Na+]>Cl.C(O)C.O.C(Cl)Cl>[NH2:4][C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[CH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:12]=1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 14096962HCID 14096962, compound

Product 1

HCID 14096963HCID 14096963, compoundYield 69.5%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(o-acetamidobenzyl)-4-(4-pyridyl)thiazole (2.30 g, 0.007 mol) in concentrated hydrochloric acid (2 mL) and ethanol (3 mL) was refluxed for 3 hours, allowed to cool, diluted with water (2 mL) and methylene chloride (5 mL), and basified with 2.5N sodium hydroxide. The layers were separated with the aqueous layer reextracted with chloroform (2x). The combined organic extracts were dried over potassium carbonate, concentrated, and chromatographed through a short column of silica gel to afford 2-(o-aminobenzyl)-4-(4-pyridyl)thiazole (1.30 g, 65%). mp. 179°-181° C. dec.

Workup

  1. temperatureto cool
  2. customThe layers were separated with the aqueous layer
  3. dry with materialThe combined organic extracts were dried over potassium carbonate
  4. concentrationconcentrated
  5. customchromatographed through a short column of silica gel

Sources & evidence

ORD record
ord-01fa80306865499fa787ebe5005a2c4f
Source dataset
uspto-grants-1988_02
Patent number
US04725606

Reaction notes

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