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

HRID 78486

Reaction equation

HRID 78486 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
  8. washThe residue was washed with a small amount of ethyl acetate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-3697807c9d7c4d5d9ac0188335d27475
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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