Aminoacetaldehyde dimethyl acetal → HCID 19699290, compound

HRID 863067Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH2:8][CH:7]([N:13]=[C:14]=[S:15])[CH2:6][CH2:5]2.CO[CH:18](OC)[CH2:19][NH2:20]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH2:8][CH:7]([N:13]1[CH:18]=[CH:19][NH:20][C:14]1=[S:15])[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of (-)-6,7-difluoro-2-isothiocyano-1,2,3,4-tetrahydronaphthalene (0.49 g, 2.2 mmol), prepared as in Example 10, and 2,2-dimethoxyethylamine (0.23 g, 2.2 mmol) in DMF was heated at 85° C. under argon for 2.5 hours. The solvent was removed under reduced pressure and the residue was dissolved in 2 to 3 mL of ethanol and 20 mL of 4N hydrochloric acid. The solution was heated at 85° C. for approximately 48 hours and cooled giving a crystalline material. The material was isolated by filtration and dried. Purification by column chromatography on silica gel (elution: 3% methanol/methylene chloride) gave (-)-6,7-difluoro-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (0.225 g, 0.84 mmol), m.p. 200°-205° C. [α]D25 -77.9°, (c=0.6, 2:1 CHCl3 /CH3 OH).

Workup

customThe solvent was removed under reduced pressure
dissolutionthe residue was dissolved in 2 to 3 mL of ethanol
temperatureThe solution was heated at 85° C. for approximately 48 hours
temperaturecooled
customgiving a crystalline material
customThe material was isolated by filtration
customdried
customPurification by column chromatography on silica gel (elution: 3% methanol/methylene chloride)

Sources & evidence

ORD record: ord-4301d048a45146ddbc4a413722a97dae
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719280

Reaction notes

Loading…