Reaction equation
[C:1]12([NH:11][C:12]#[N:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[ClH:14].[I:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18]>>[ClH:14].[C:1]12([NH:11][C:12]([NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[I:15])=[NH:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2Participants
Procedure
Adamantan-1-ylcyanamide (299 mg, 1.70 mmol) and o-iodoaniline hydrochloride (433 mg 1.70 mmol) were finely ground together and heated at 200° for 10 min. The resultant black glassy solid was pulverized, and recrystallized 5 times from EtOH/Et2O. The resultant faintly blue needles (80 mg) were dissolved in 4 ml EtOH, and passed through a short (<1 cm) column packed from bottom to top with Celite, charcoal, activated alumina, and sand. The colorless eluate was then diluted with 5 ml Et2O, and allowed to stand in an Et2O diffusion chamber overnight. The white needles were collected by suction filtration, 40 mg, mp 274°-275° C. Addition of another 5 ml Et2O yielded a second crop (31 mg) of identical material. Combined yield: 21%. 1H (CD3OD) δ1.779 (s, 6H), 2.090 (s, 6H), 2.164 (s, 3H), 7.168 (t, 1H, J=8.1 Hz), 7.388 (d, 1H, J=9.1 Hz), 7.503 (t, 1H, J=7.8 Hz), 8.004 (d, 1H, J=7.8 Hz).
Workup
- temperatureheated at 200° for 10 min
- customrecrystallized 5 times from EtOH/Et2O
- dissolutionThe resultant faintly blue needles (80 mg) were dissolved in 4 ml EtOH
- additionThe colorless eluate was then diluted with 5 ml Et2O
- customto stand in an Et2O diffusion chamber overnight
- filtrationThe white needles were collected by suction filtration, 40 mg, mp 274°-275° C
- additionAddition of another 5 ml Et2O
Sources & evidence
- ORD record
- ord-fe557825bef742ea8bbd15fc5f607c0f
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05574070
Linked notes
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