3-amino-4-hydroxy-N-(1-propylbutyl)benzamide → N-(heptan-4-yl)-2-(methylthio)benzo[d]oxazole-5-carboxamide

HRID 339343Notes

Reaction equation

[CH3:1][CH2:2][CH2:3][CH:4]([NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17]([SH:19])=[N:16][C:15]=2[CH:20]=1)=[O:10])[CH2:5][CH2:6][CH3:7].N[C:22]1C=C(C=CC=1O)C(NC(CCC)CCC)=O>CCO>[CH3:7][CH2:6][CH2:5][CH:4]([NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17]([S:19][CH3:22])=[N:16][C:15]=2[CH:20]=1)=[O:10])[CH2:3][CH2:2][CH3:1]

Participants

Conditions

Temperature: 80 °C

Procedure

N-(Heptan-4-yl)-2-(mercapto)benzo[d]oxazole-5-carboxamide: To a solution 3-amino-4-hydroxy-N-(1-propylbutyl)benzamide (example 41a) (250 mg, 1.0 mmol) in EtOH was added KSCSOEt (160 mg, 1.0 mmol). The resulting reaction mixture was heated at 80° C. overnight. The solvent was removed under reduced pressure. And the residue was taken up in water. The resulting mixture was acidified with HOAc to pH ˜5 and then filtered. The residue was washed with water to afford the product as a white solid (160 mg, 55%). MS (M+H, 293.1).

Workup

customThe resulting reaction mixture
customThe solvent was removed under reduced pressure
filtrationfiltered
washThe residue was washed with water

Sources & evidence

ORD record: ord-91914baf27bd4fb09880c9ae808d1015
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895050B2

Reaction notes

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