5-Chloro-o-anisic acid → 5-chloro-N-(5-chlorothiazol-2-yl)-2-methoxybenzamide

HRID 1037907Notes

Reaction equation

HRID 1037907 reaction equation
Cl.[Cl:2][C:3]1[S:7][C:6]([NH2:8])=[N:5][CH:4]=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.O.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:8][C:6]1[S:7][C:3]([Cl:2])=[CH:4][N:5]=1)=[O:16]

Participants

7

Reactant 4

HCID 769705-Chloro-o-anisic acidHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

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 5-chlorothiazol-2-amine hydrochloride (513 mg, 3 mmol, 5-chloro-2-methoxybenzoic acid (670 mg, 3.6 mmol, 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (1.15 g, 6 mmol), 1-hydroxybenzotriazole hydrate (810 mg, 6 mmol) and 4-(dimethylamino)pyridine (73 mg, 0.6 mmol) in pyridine was stirred at room temperature for 2 hours. The volatiles were removed under vacuum, and the resulting mixture was diluted with water and extracted with ethyl acetate. The organic extract was dried (Na2SO4), filtered and concentrated The residue was washed with a small amount of ethyl acetate, and filtered to afford the title compound. MS (ESI) m/z 303 (M+H)+.

Workup

  1. customThe volatiles were removed under vacuum
  2. additionthe resulting mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated The residue
  8. washwas washed with a small amount of ethyl acetate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-4336be629acd41488bb20b60edbb1696
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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