Methanamine, N-methoxy-, hydrochloride (1:1) → N-Methoxy-N-methyl-2-oxazol-2-yl-benzamide

HRID 419113Notes

Reaction equation

HRID 419113 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].CCN(C(C)C)C(C)C.Cl.[CH3:25][NH:26][O:27][CH3:28]>C(Cl)Cl>[CH3:28][O:27][N:26]([CH3:25])[C:8](=[O:9])[C:7]1[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=1[C:2]1[O:1][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 213136652-Oxazol-2-yl-benzoyl chloride

Product 1

HCID 57942199N-Methoxy-N-methyl-2-oxazol-2-yl-benzamideYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-Oxazol-2-yl-benzoyl chloride (104 mg, 0.5 mmol), DIEA (0.26 mL, 1.5 mmol) in 2 ml of DCM was added N,O-dimethylhydroxylamine hydrochloride (59 mg, 0.6 mmol). The mixture was stirred at room temperature for 2 hours, washed with dilute HCl solution followed by brine. Concentration of the organic layer afforded 100 mg of N-Methoxy-N-methyl-2-oxazol-2-yl-benzamide as a sticky light yellow liquid. MS: (M+H)/z=233.1.

Workup

  1. washwashed with dilute HCl solution

Sources & evidence

ORD record
ord-9376af1098b340db9ff43732b70f0028
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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