1-Adamantylcyanamide → N-(Adamantan-1-yl)-N'-(2-iodophenyl)guanidine HCl

HRID 1441172Notes

Reaction equation

HRID 1441172 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]2

Participants

3

Reactant 2

HCID 124358461-AdamantylcyanamideHCID 15621116o-Iodoaniline hydrochloride

Product 1

HCID 178479307N-(Adamantan-1-yl)-N'-(2-iodophenyl)guanidine HClYield 21%

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 5ml 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) 1.779 (s, 6H), 2.090 (s, 6H), 2.164 (s, 3 H), 7.168 (t, 1H, J=8.1 Hz), 7.388 (d, 1 H, J=9.1 Hz), 7.503 (t, 1 H, J=7.8 Hz), 8.004 (d, 1 H, J=7.8 Hz).

Workup

  1. temperatureheated at 200° for 10 min
  2. customrecrystallized 5 times from EtOH/Et2O
  3. dissolutionThe resultant faintly blue needles (80 mg) were dissolved in 4 ml EtOH
  4. additionThe colorless eluate was then diluted with 5ml Et2O
  5. customto stand in an Et2O diffusion chamber overnight
  6. filtrationThe white needles were collected by suction filtration, 40 mg, mp 274°-275° C
  7. additionAddition of another 5 ml Et2O

Sources & evidence

ORD record
ord-81011f7b9b98449fb8cf24c9eea5afd8
Source dataset
uspto-grants-1996_03
Patent number
US05502255

Reaction notes

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