4-Acetylbenzoic acid p-nitrophenyl ester → HCID 15895998, compound

HRID 1954192Notes

Reaction equation

[N+](C1C=CC(O[C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=2)=CC=1)([O-])=O.[NH2:22][C:23]1[S:24][CH:25]=[C:26]([C:28]([NH:30][CH2:31][CH2:32][N:33]([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])=[O:29])[N:27]=1>>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([C:11]([NH:22][C:23]2[S:24][CH:25]=[C:26]([C:28]([NH:30][CH2:31][CH2:32][N:33]([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:35])[CH3:36])=[O:29])[N:27]=2)=[O:21])=[CH:17][CH:16]=1)(=[O:20])[CH3:19]

Participants

Reactant 2

HCID 158959964-Acetylbenzoic acid p-nitrophenyl ester

HCID 15895997HCID 15895997, compound

Product 1

HCID 15895998HCID 15895998, compoundYield 57.1%

Conditions

Temperature: 130 °C

Procedure

To 831 mg of 4-acetylbenzoic acid p-nitrophenyl ester, 788 mg of 2-amino-4-[(2-diisopropylaminoethyl)aminocarbonyl]-1,3-thiazole were added. The resulting mixture was stirred at 130° C. for 8 hours. The reaction mixture was purified by column chromatography on NH silica gel (chloroform), whereby 693 mg of 2-[N-(4-acetylbenzoyl)amino]-4-[(2-diisopropylaminoethyl)aminocarbonyl]-1,3-thiazole were obtained. After 2 ml of a 4N hydrochloric acid--dioxane solution were added to the resulting compound, the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of isopropyl ether and ethanol, whereby 395 mg of the title compound were obtained as yellow powder.

Workup

customThe reaction mixture was purified by column chromatography on NH silica gel (chloroform)

Sources & evidence

ORD record: ord-ea2b3a078ac04453be0439eb19303e32
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121301

Reaction notes

Loading…