Formamidine acetate → 6-[(4-Chlorophenyl)-(1,2,4-triazol-1-yl)methyl]-1-methylbenzotriazole

HRID 1376823ノート

反応式

HRID 1376823 の反応式
[ClH:1].ClC1C=C[C:6]([NH:9][NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]3[N:19]=[N:18][N:17]([CH3:20])[C:16]=3[CH:21]=2)=CC=1.[C:22](O)(=O)[CH3:23].[CH:26](=[NH:28])N>CO>[Cl:1][C:22]1[CH:23]=[CH:16][C:21]([CH:11]([N:10]2[CH:26]=[N:28][CH:6]=[N:9]2)[C:12]2[CH:13]=[CH:14][C:15]3[N:19]=[N:18][N:17]([CH3:20])[C:16]=3[CH:21]=2)=[CH:12][CH:11]=1

参加物

4

反応物 2

HCID 160693Formamidine acetateHCID 18924324(+)-6-[(4-chlorophenyl)hydrazinomethyl]-1-methyl-1H-benzotriazole monohydrochloride

生成物 1

HCID 607966-[(4-Chlorophenyl)-(1,2,4-triazol-1-yl)methyl]-1-methylbenzotriazole収率 131.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 5 g of intermediate 4-a, 4.8 g of methanimidamide monoacetate and 15 ml of methanol was stirred for 1.5 hours at reflux temperature. After cooling to room temperature, the reaction mixture crystallized and there were added 30 ml of water. After stirring for 1 hour the precipitate was filtered off, washed with water and dried in vacuo at 50° C. The product was diluted with 11.8 ml of 2-propanol and the whole was treated with active charcoal for 15 min. at reflux temperature. The charcoal was filtered off while hot and washed with 2-propanol. The product was crystallized, filtered off and dried in vacuo at 50° C., yielding 3.3 g (66.0%) of (+)-6-[(4-chlorophenyl)-(1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole (comp. 1-a); mp. 130°-135° C.; [α]D20 =+8.0° (conc.=10% in CH3OH); enantiomeric excess: 98.4%.

後処理

  1. temperatureat reflux temperature
  2. customthe reaction mixture crystallized
  3. additionthere were added 30 ml of water
  4. stirringAfter stirring for 1 hour the precipitate
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried in vacuo at 50° C
  8. additionThe product was diluted with 11.8 ml of 2-propanol
  9. additionthe whole was treated with active charcoal for 15 min.
  10. temperatureat reflux temperature
  11. filtrationThe charcoal was filtered off while hot and
  12. washwashed with 2-propanol
  13. customThe product was crystallized
  14. filtrationfiltered off
  15. customdried in vacuo at 50° C.

出典と根拠

ORDレコード
ord-ec000bd974d24d0198bd8f7632827eab
出典データセット
uspto-grants-1997_09
特許番号
US05663354

反応ノート

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