Hexamethylenetetramine → HCID 86683416, compound
Reaction equation
C([O:3][C:4](=[O:20])[CH2:5][CH2:6][C:7]1[C:8](=[O:19])[O:9][C:10]2[C:15]([C:16]=1[CH3:17])=[CH:14][CH:13]=[C:12]([OH:18])[CH:11]=2)C.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:33](O)=[O:34]>>[CH:33]([C:11]1[C:12]([OH:18])=[CH:13][CH:14]=[C:15]2[C:10]=1[O:9][C:8](=[O:19])[C:7]([CH2:6][CH2:5][C:4]([OH:3])=[O:20])=[C:16]2[CH3:17])=[O:34]Participants
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 3-(7-hydroxy-4-methyl-2-oxo-2H-chromen-3-yl)-propionic acid ethyl ester (100 mg, 0.36 mmol) and hexamethylenetetramine (203 mg, 1.44 mmol) in trifluoroacetic acid (3.6 mL) was stirred in a closed vial under argon at 110° C. for 2 h. The reaction was poured onto crushed ice (15 mL), warmed to room temperature, and the solid precipitate was filtered off. This mixture of formylated ester and corresponding carboxylic acid was dissolved in dioxane-1N NaOH (1:1) and was stirred at room temperature. After 2 h, 15 mL of dichloromethane was added. The aqueous layer was separated and acidified by portionwise addition of 1N HCl. The precipitate was collected, washed with water, and dried to afford title compound (15 mg, 0.043 mmol, 13%) as a light brown powder.
Workup
- additionThe reaction was poured
- temperaturewarmed to room temperature
- filtrationthe solid precipitate was filtered off
- additionThis mixture of formylated ester and corresponding carboxylic acid
- dissolutionwas dissolved in dioxane-1N NaOH (1:1)
- stirringwas stirred at room temperature
- waitAfter 2 h
- addition15 mL of dichloromethane was added
- customThe aqueous layer was separated
- additionacidified by portionwise addition of 1N HCl
- customThe precipitate was collected
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-32e182ecb1624f4db2b7936491b8921d
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040714B2
Reaction notes
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