Ethanol → HCID 136386398, compound

HRID 1977313Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3=[N:13][C:14]([C:16]4[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=4)=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.O.[CH2:31](O)[CH3:32]>>[CH2:31]([O:21][C:20](=[O:22])[C:19]1[CH:23]=[CH:24][C:16]([C:14]2[N:13]=[C:11]3[N:10]([CH:15]=2)[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[S:12]3)=[CH:17][CH:18]=1)[CH3:32]

Participants

Reactant 4

HCID 702Ethanol

HCID 962Water

HCID 1118Sulfuric Acid

HCID 135815285HCID 135815285, compound

Product 1

HCID 136386398HCID 136386398, compound

Conditions

Temperature: 80 °C

Procedure

To a suspension of 4-[2-(4-hydroxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid (4.0 g) in ethanol (50 ml) was added sulfuric acid (1.0 ml) and the mixture was stirred at 80° C. for 9 hours. The reaction mixture was pulverized with water. The precipitate was collected by filtration, washed with water, acetonitrile and diisopropyl ether and dried to give 4-[2-(4-hydroxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid ethyl ester (2.09 g).

Workup

filtrationThe precipitate was collected by filtration
washwashed with water, acetonitrile and diisopropyl ether
customdried

Sources & evidence

ORD record: ord-2b279e6c59fe43ff88f519fdca134456
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06232290B1

Reaction notes

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