Thionyl Chloride → HCID 67549048, compound

HRID 43613Notes

Reaction equation

HRID 43613 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=O)[NH:5][C:6]=1[CH2:7][CH3:8].S(Cl)(Cl)=O.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:24][C:25]([CH3:32])=[C:26]([C:28]([O:30][CH3:31])=[O:29])[N:27]=2)=[CH:19][C:18]=1[O:33][CH3:34]>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[O:24][C:25]([CH3:32])=[C:26]([C:28]([O:30][CH3:31])=[O:29])[N:27]=3)=[CH:19][C:18]=2[O:33][CH3:34])=[O:11])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 67549647Methyl 2-(4-amino-3-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylate

Product 1

HCID 67549048HCID 67549048, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The same operation as in Example (91c) was performed using 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (0.135 g, 0.78 mmol), thionyl chloride (4 mL), methyl 2-(4-amino-3-methoxyphenyl)-5-methyl-1,3-oxazole-4-carboxylate obtained in Example (105d) (0.3 g, 1.03 mmol) and pyridine (5 mL), to obtain 0.23 g of the title compound as a colorless solid (71%).

Sources & evidence

ORD record
ord-9b92eb25a7d14c16855211644459e0d8
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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