1-Hydroxybenzotriazole → 5-chloro-N-(5-chlorothiazol-2-yl)-2-methoxybenzamide

HRID 1037919Notes

Reaction equation

HRID 1037919 reaction equation
Cl.[NH2:2][C:3]1[S:4][C:5]([Cl:8])=[CH:6][N:7]=1.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=1)[C:15](O)=[O:16].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=1)[C:15]([NH:2][C:3]1[S:4][C:5]([Cl:8])=[CH:6][N:7]=1)=[O:16]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 769705-Chloro-o-anisic acidHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 866189125-chloro-N-(5-chlorothiazol-2-yl)-2-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 2-amino-5-chlorothiazole hydrochloric acid (1.0 g, 5.9 mmol), 5-chloro-2-methoxybenzoic acid (1.3 g, 7.0 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (Chem-Impex International, 2.2 g, 12 mmol), 1-hydroxybenzotriazole (0.95 g, 7.0 mmol) and 4-dimethylaminopyridine (0.14 g, 1.2 mmol) in 6 mL of pyridine was allowed to stir at ambient temperature for 72 hours. The reaction mixture was concentrated under reduced pressure and 10 mL of H2O was added. The resulting solids were isolated by filtration, washed with 5 mL of H2O and twice with 5 mL of ethyl acetate, and dried to afford the title compound. MS (DCI/NH3) m/Z 303 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and 10 mL of H2O
  2. additionwas added
  3. customThe resulting solids were isolated by filtration
  4. washwashed with 5 mL of H2O and twice with 5 mL of ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-1943ce5adf034eb19856b210091f4741
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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