Hydrochloric Acid → HCID 54757215, compound

HRID 1782157Notes

Reaction equation

HRID 1782157 reaction equation
[NH2:1][C:2]1[C:3]([CH3:10])=[N:4][S:5][C:6]=1[C:7]([OH:9])=[O:8].[C:11](Cl)(=O)[CH2:12][CH2:13][CH3:14].Cl>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:10][C:3]1[C:2]2[N:1]=[C:11]([CH2:12][CH2:13][CH3:14])[O:8][C:7](=[O:9])[C:6]=2[S:5][N:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8855Butyryl chlorideHCID 228318524-Amino-3-methyl-1,2-thiazole-5-carboxylic acid

Product 1

HCID 54757215HCID 54757215, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-amino-3-methyl-isothiazole-5-carboxylic acid (method 57) (2.91 g, 15 mmol) in pyridine (20 mL) at 0° C., was added dropwise a solution of butyryl chloride (3.18 g, 30 mmol) in chloroform (30 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. Chloroform (200 mL) was added to the reaction mixture followed by 2M HCl (200 mL) and the mixture was stirred. The chloroform layer was further washed with 2M HCl (100 mL), water (100 mL), brine (100 mL) and concentrated. Column purification of the thus obtained crude product provided the pure product as light brown solid. Yield 2 g (64%). 1H NMR (300 MHz) δ 1.03 (t, 3H), 1.80-1.92 (m, 2H), 2.65 (s, 3H), 2.76 (t, 2H).

Workup

  1. stirringthe mixture was stirred
  2. washThe chloroform layer was further washed with 2M HCl (100 mL), water (100 mL), brine (100 mL)
  3. concentrationconcentrated
  4. customColumn purification of the
  5. customthus obtained crude product

Sources & evidence

ORD record
ord-6b91ab75ac094a7e9ecc0cda3af0ec4a
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

Loading…