Hydrochloric Acid → 2-Amino-5-[(3-carbomethoxyphenyl)thio]thiazole

HRID 1294745Notes

Reaction equation

HRID 1294745 reaction equation
C[O-].[Na+].Cl.[NH2:5][C:6]1[S:7][C:8](Br)=[CH:9][N:10]=1.[C:12]([C:15]1[CH:16]=[C:17]([SH:21])[CH:18]=[CH:19][CH:20]=1)([OH:14])=[O:13].Cl.O1CCOC[CH2:24]1>CO>[CH3:24][O:13][C:12](=[O:14])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([S:21][C:8]2[S:7][C:6]([NH2:5])=[N:10][CH:9]=2)[CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 95737Benzoic acid, 3-mercapto-HCID 10942334Sodium MethoxideHCID 221703925-Bromo-1,3-thiazol-2-amine--hydrogen chloride (1/1)

Product 1

HCID 222883712-Amino-5-[(3-carbomethoxyphenyl)thio]thiazoleYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 4.37 M solution of sodium methoxide in methanol (10 mL, 43.7 mmol) was added dropwise to a stirred suspension of 2-amino-5-bromothiazole hydrochloride (2.16 g, 10 mmol) and 3-carboxythiophenol (1.85 g, 12 mmol) in methanol (75 mL) at 0-5° C. The solution was allowed to warm to rt. for 2 h and a 4 M solution of hydrogen chloride in dioxane (15 mL, 60 mmol) was added. The suspension was stirred at rt. overnight and concentrated. The crude residue was diluted with satd. aqueous sodium bicarbonate solution (50 mL). The precipitated solid was filtered and washed with water (20 mL, 5×) and ether (20 mL, 5×). The solid was filtered and dried in vacuo at 60° C. to obtain the titled compound (1.97 g, 75%).

Workup

  1. concentrationovernight and concentrated
  2. additionThe crude residue was diluted with satd
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water (20 mL, 5×) and ether (20 mL, 5×)
  5. filtrationThe solid was filtered
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-9103846739924a46a3cdc18159e853bb
Source dataset
uspto-grants-2007_07
Patent number
US07241781B2

Reaction notes

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