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

HRID 1770253

反応式

HRID 1770253 の反応式
[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

参加物

3

反応物 2

HCID 124358461-AdamantylcyanamideHCID 15621116o-Iodoaniline hydrochloride

生成物 1

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

実験手順

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, 3H), 7.168 (t, 1 H, 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).

後処理

  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

出典と根拠

ORDレコード
ord-e25f98daafb349fd8b10e200f22ef996
出典データセット
uspto-grants-1995_01
特許番号
US05385946

関連ノート

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