Dimethylformamide → 1-[(3-fluorophenyl)methyl]-1H-benzimidazol-2-amine

HRID 979904ノート

反応式

HRID 979904 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH2:10].CN(C)C=O.[H-].[Na+].Cl[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1>O.CC1C=CC=CC=1>[F:26][C:22]1[CH:21]=[C:20]([CH2:19][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[NH2:10])[CH:25]=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 6228Dimethylformamide2 回HCID 99743-Fluorobenzyl chlorideHCID 136242-AminobenzimidazoleHCID 24758Sodium hydride

生成物 1

HCID 137696381-[(3-fluorophenyl)methyl]-1H-benzimidazol-2-amine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
40 °C

実験手順

To a stirred and heated (60° C.) solution of 41.3 parts of 1H-benzimidazol-2-amine in 162 parts of N,N-dimethylformamide (DMF) were added portionwise during a 40 minutes period 12 parts of sodium hydride dispersion 60%. Upon completion, stirring at 60° C. was continued for 30 minutes. After cooling to 40° C., there was added dropwise during 25 minutes a solution of 50 parts of 1-(chloromethyl)-3-fluorobenzene in 9 parts of DMF and 36 parts of methylbenzene. After the addition was complete, the whole was stirred for 1.50 hours at 50°-65° C. The reaction mixture was cooled and water was added. The solid product was filtered off and crystallized from a mixture of 2,2'-oxybispropane, tetrahydrofuran and methanol. The product was filtered off and recrystallized from methylbenzene, yielding 34.8 parts of 1-[(3-fluorophenyl)methyl]-1H-benzimidazol-2-amine; mp. 188.1° C. (1).

後処理

  1. stirringUpon completion, stirring at 60° C.
  2. additionAfter the addition
  3. stirringthe whole was stirred for 1.50 hours at 50°-65° C
  4. temperatureThe reaction mixture was cooled
  5. filtrationThe solid product was filtered off
  6. customcrystallized from a mixture of 2,2'-oxybispropane, tetrahydrofuran and methanol
  7. filtrationThe product was filtered off
  8. customrecrystallized from methylbenzene

出典と根拠

ORDレコード
ord-a34f807c488149b3b2e7fd0052a5c784
出典データセット
uspto-grants-1987_01
特許番号
US04634704

反応ノート

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