Triethylamine → 3-Methyl-2-(5-(phthalimido)pentan-1-ylthio]-1,4,7b-triazacyclopent[cd]indene

HRID 1068805Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7](=[S:13])[NH:8]3.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].C(N(CC)CC)C>CN(C)C=O>[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7]([S:13][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:21](=[O:30])[C:22]2=[CH:29][CH:28]=[CH:27][CH:26]=[C:23]2[C:24]1=[O:25])=[N:8]3

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 2.03 g (10.7 mmol) of 1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-thione in 50 ml of N,N-dimethylformamide were added 3.18 g (10.7 mmol) of N-(5-bromopentyl)phthalimide and 2.24 ml (16.1 mmol) of triethylamine. The mixture was stirred for two hours at 100° C. After cooling, the resulting precipitates were collected by filtration, washed with N,N-dimethylformamide, ethanol, and diethylether, successively, dried to afford 3.44 g of the desired compound (79.3%, a pale brown solid).

Workup

temperatureAfter cooling
customthe resulting precipitates
filtrationwere collected by filtration
washwashed with N,N-dimethylformamide, ethanol, and diethylether
customsuccessively, dried

Sources & evidence

ORD record: ord-8ebc78c29e554ef2b3a6d6315e006581
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251905B1

Reaction notes

Loading…