Hydrochloric Acid → HCID 76571403, compound

HRID 2109507Notes

Reaction equation

HRID 2109507 reaction equation
[C:1]([NH:9][C:10](=[CH:15][N:16]([CH3:18])C)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC1[S:21][CH:22]=[CH:23][N:24]=1.Cl.O>C(O)(C)C>[C:1]([NH:9][C:10](=[CH:15][NH:16][C:18]1[S:21][CH:22]=[CH:23][N:24]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21552-AminothiazoleHCID 3644677HCID 3644677, compound

Product 1

HCID 76571403HCID 76571403, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10g (39.5 mmol) of methyl 2-benzoylamino-3-dimethylaminoacrylate and 11.3 g (118 mmol) of 2-aminothiazole were dissolved at 40° C. in 200 ml of isopropanol. The solution was admixed with 3.96 ml (48 mmol) of concentrated hydrochloric acid within 5 minutes (min) and stirred for a further 60 min. 75 ml of deionized water were added, the suspension was cooled overnight and the crystallized product was filtered off. Yield: 8.6 g (70% of theory) 1H NMR: 3.62 (s, 3H); 7.08 (d, 1H); 7.32 (d, 1H); 7.45-7.60 (m, 3H); 8.02 (d, 2H); 8.22 (d, 1 H); 9.28 (s, 1 H); 10.45 (d, 1 H)

Workup

  1. temperaturethe suspension was cooled overnight
  2. filtrationthe crystallized product was filtered off

Sources & evidence

ORD record
ord-2599c8ce777340a2af17ad314b01f6df
Source dataset
uspto-grants-2009_04
Patent number
US07514578B2

Reaction notes

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