Tetramethyl orthocarbonate → 2-Methoxy-benzooxazole-5-carboxylic Acid (1-propyl-butyl)-amide

HRID 339341

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[OH:18])[C:5]([NH:7][CH:8]([CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10][CH3:11])=[O:6].[CH3:19][O:20][C:21](OC)(OC)OC>>[CH2:9]([CH:8]([NH:7][C:5]([C:4]1[CH:15]=[CH:16][C:17]2[O:18][C:19]([O:20][CH3:21])=[N:1][C:2]=2[CH:3]=1)=[O:6])[CH2:12][CH2:13][CH3:14])[CH2:10][CH3:11]

Participants

Reactant 2

HCID 74613Tetramethyl orthocarbonate

HCID 667731203-amino-4-hydroxy-N-(1-propylbutyl)benzamide

Product 1

HCID 575279892-Methoxy-benzooxazole-5-carboxylic Acid (1-propyl-butyl)-amideYield 60%

Procedure

Prepared in a similar manner to example 41 using 3-amino-4-hydroxy-N-(1-propylbutyl)benzamide (example 41a) and tetramethylorthocarbonate. Yield: 60%. mp 137-138° C.; MS (M+H, 291.10).

Sources & evidence

ORD record: ord-9e42a0aa231c471187e6b56d3954802d
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895050B2

Linked notes

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