Benzoyl chloride → N-[5-[[(5-ethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]benzamide

HRID 1637238Notes

Reaction equation

HRID 1637238 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:8][C:9]2[O:10][C:11]([CH2:14][CH3:15])=[CH:12][N:13]=2)=[CH:5][N:6]=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:14]([C:11]1[O:10][C:9]([CH2:8][S:7][C:4]2[S:3][C:2]([NH:1][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:6][CH:5]=2)=[N:13][CH:12]=1)[CH3:15]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 186679822-Amino-5-[[(5-ethyl-2-oxazolyl)methyl]thio]-thiazole

Product 1

HCID 9906190N-[5-[[(5-ethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]benzamideYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-amino-5-[[(5-ethyl-2-oxazolyl)methyl]thio]-thiazole (48.2 mg, 0.2 mmol), benzoyl chloride (24.4 mg, 0.21 mmol) and triethylamine (35 mg, 0.35 mmol) in methylene chloride (0.5 mL) was stirred at rt for 10 min. The organic solution was washed with water and concentrated. The residue was purified by a flash column (SiO2 ; hexanes: ethyl acetate/2:1) to afford N-[5-[[(5-ethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]benzamide (41 mg, 59%) as a solid, mp 122-123° C. 1H NMR (CDCl3) δ12.65 (s, 1 H), 7.96 (m, 2 H), 7.61 (m,, 1 H), 7.49 (m, 2 H), 6.88 (s, 1 H), 6.56 (s, 1 H), 3.93 (s, 2 H), 2.61 (q, J=7.6 Hz, 2 H), 1.20 (t, J=7.6 Hz, 3 H); MS m/e 346 (M+H)+ ;

Workup

  1. washThe organic solution was washed with water
  2. concentrationconcentrated
  3. customThe residue was purified by a flash column (SiO2 ; hexanes: ethyl acetate/2:1)

Sources & evidence

ORD record
ord-32e2c3bea13f4b82892149a20741cd1b
Source dataset
uspto-grants-2000_03
Patent number
US06040321

Reaction notes

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