Pent-4-yn-1-amine → N-Cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-N"-(4-pentyn-1-yl)guanidine

HRID 236712

반응식

HRID 236712 반응식
[C:1]([NH:3][C:4](=[N:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])SC)#[N:2].[CH2:18]([NH2:23])[CH2:19][CH2:20][C:21]#[CH:22]>C(#N)C>[C:1]([NH:3][C:4]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12]1[NH:16][CH:15]=[N:14][C:13]=1[CH3:17])=[N:23][CH2:18][CH2:19][CH2:20][C:21]#[CH:22])#[N:2]

참가 물질

4

반응물 2

HCID 641001Pent-4-yn-1-amineHCID 178503877HCID 178503877, 화합물

생성물 1

HCID 178446439N-Cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-N"-(4-pentyn-1-yl)guanidine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of N-cyano-N'-{2-[(4-methyl-5-imidazolyl)methylthio]ethyl}-S-methylisothiourea (3.00 g., 0.0111 mole) and 4-pentyn-1-amine (3.69 g., 0.0445 mole) in 60 ml. of acetonitrile was stirred at reflux for 24 hours, and then allowed to stand at room temperature for 96 hours. The solvent and excess amine were removed under reduced pressure and the residual yellow gum was purified by chromatography on 50 g. of 100-200 mesh silica gel, using gradient elution with methylene chloride/methanol (99:1-96:4). The middle fractions indicated by TLC to be pure were combined and evaporated to give 1.91 g. of yellow gum which was crystallized at -15° C. from 18 ml. of ethyl acetate. The resulting white solid (1.25 g.) was recrystallized at -15° C. from 10 ml. of acetonitrile to give 1.063 g. of product; m.p. 99°-103° C.

후처리

  1. temperatureat reflux for 24 hours
  2. customThe solvent and excess amine were removed under reduced pressure
  3. customthe residual yellow gum was purified by chromatography on 50 g
  4. washelution with methylene chloride/methanol (99:1-96:4)
  5. customevaporated
  6. customto give 1.91 g
  7. customof yellow gum which was crystallized at -15° C. from 18 ml
  8. customThe resulting white solid (1.25 g.) was recrystallized at -15° C. from 10 ml
  9. customof acetonitrile to give 1.063 g

출처 및 근거

ORD 기록
ord-22909f4230cb4d73965aefc973ee9185
출처 데이터셋
uspto-grants-1979_06
특허 번호
US04157347

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