Sodium Hydroxide → 2-Amino-5-[(3-carbomethoxyphenyl)thio]thiazole

HRID 968196Notes

Reaction equation

HRID 968196 reaction equation
[OH-].[Na+].C(OC([NH:10][C:11]1[S:12][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([O:25][CH3:26])=[O:24])[CH:18]=2)=[CH:14][N:15]=1)=O)(C)(C)C>CO.C1COCC1>[CH3:26][O:25][C:23](=[O:24])[C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([S:16][C:13]2[S:12][C:11]([NH2:10])=[N:15][CH:14]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 221704102-Tert-butoxycarbonylamino-5-[(3-carbomethoxyphenyl)thio]thiazole

Product 1

HCID 222883712-Amino-5-[(3-carbomethoxyphenyl)thio]thiazole

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 1 N aqueous sodium hydroxide solution (50 mL, 50 mmol) was added dropwise to a stirred solution of 2-tert-butoxycarbonylamino-5-[(3-carbomethoxyphenyl)thio]thiazole (1.8 g, (contaminated with bis(tert-butoxycarbonyl)amino adduct)) in a methanol-THF mixture (160 mL, 3:1). The solution was stirred at rt. for 24 h and concentrated. The residue was acidified with 2 N aqueous HCl (30 mL) and the suspension was extracted with dichloromethane-methanol mixture (120 mL, 3:1, 2×). The combined organic extract was dried (MgSO4), filtered and concentrated in vacuo to obtain the titled compound (1.32 g, 75% overall yield from Example 1, part A) as an off-white solid. D. 5-[[3-[(4-Acetylpiperazin-1-yl)carbonyl]phenyl]thio]thiazol-2-ylcarbamic acid 1,1-(dimethylethyl) ester

Workup

  1. concentrationconcentrated
  2. extractionthe suspension was extracted with dichloromethane-methanol mixture (120 mL, 3:1, 2×)
  3. extractionThe combined organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77d46f1356d34d93b02fb60923e3f331
Source dataset
uspto-grants-2005_10
Patent number
US06958336B2

Reaction notes

Loading…