Sulfuric Acid → 6-(4-Isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)thieno[2,3-b]pyridine-5-carboxylic acid

HRID 256122Notes

Reaction equation

[C:1]([C:4]([NH:9][C:10]([C:12]1[N:17]=[C:16]2[S:18][CH:19]=[CH:20][C:15]2=[CH:14][C:13]=1[C:21]([OH:23])=[O:22])=O)([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2].[OH-].[Na+].OS(O)(=O)=O>O>[CH:5]([C:4]1([CH3:8])[C:1](=[O:3])[NH:2][C:10]([C:12]2[N:17]=[C:16]3[S:18][CH:19]=[CH:20][C:15]3=[CH:14][C:13]=2[C:21]([OH:23])=[O:22])=[N:9]1)([CH3:7])[CH3:6]

Participants

Conditions

Temperature: 80 °C

Procedure

6-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]thieno[2,3-b]pyridine-5-carboxylic acid (17.35 g, 0.052 mol) is added to water (225 mL) containing sodium hydroxide (10.35 g, 0.26 mol). The resulting basic solution is heated at 80° C. for two hours and 45 minutes, cooled in an ice-water bath and acidified with 6N H2SO4. The product 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)thieno[2,3-b]pyridine-5-carboxylic acid is filtered off, washed with water and air dried yielding 1.54 g, 70.3%, mp 221°-223° C.

Workup

temperaturecooled in an ice-water bath
filtrationThe product 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)thieno[2,3-b]pyridine-5-carboxylic acid is filtered off
washwashed with water and air
customdried
customyielding 1.54 g, 70.3%, mp 221°-223° C.

Sources & evidence

ORD record: ord-1106f628b9904168ba39bf435e4766f4
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04701208

Reaction notes

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