Hydrochloric Acid → (+)-6-[(4-chlorophenyl)hydrazinomethyl]-1-methyl-1H-benzotriazole monohydrochloride

HRID 1288624노트

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HRID 1288624 반응식
[Cl:1]C1C=CC([C:8](=[N:19][NH:20][C:21](OC(C)(C)C)=O)[C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[N:15][N:14]([CH3:17])[C:13]=3[CH:18]=2)=CC=1.[ClH:28].O>O1CCCC1>[ClH:1].[Cl:28][C:9]1[CH:10]=[CH:11][C:21]([NH:20][NH:19][CH2:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[N:15][N:14]([CH3:17])[C:13]=3[CH:18]=2)=[CH:13][CH:18]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 867524961,1-dimethylethyl [(4-chlorophenyl)(1-methyl-1H-benzotriazol-6-yl)-methylene]hydrazine carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
22 °C

실험 절차

To a suspension of 10 g of intermediate 1-b in 60 ml of tetrahydrofuran under a nitrogen atmosphere were added dropwise over 15 minutes 26 ml of a borane tetrahydrofuran complex in tetrahydrofuran (1M). After stirring for 15 minutes at ±22° C. there were added 13 ml of hydrochloric acid (6N). The whole was heated to reflux and refluxed for 1.5 hours. The mixture was cooled to room temperature and 50 ml of water were added. After stirring for 1 hour, the reaction mixture was filtered. The filtrate was mixed with 75 ml of methylbenzene. The layers were separated and the aqueous layer was basified (pH 7.5-8) with NH4OH. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was converted into the hydrochloride salt in 2-propanol by adding 3ml of a mixture of hydrochloric acid in 2-propanol (4.8N). After stirring for 2 hours the product was filtered off, washed with 2-propanol and dried in vacuo at 50° C., yielding 2.1 g of (±)-6-[(4-chlorophenyl)hydrazinomethyl]-1-methyl-1H-benzotriazole monohydrochloride (interm. 2-e).

후처리

  1. temperatureThe whole was heated
  2. temperatureto reflux
  3. temperaturerefluxed for 1.5 hours
  4. temperatureThe mixture was cooled to room temperature
  5. stirringAfter stirring for 1 hour
  6. filtrationthe reaction mixture was filtered
  7. additionThe filtrate was mixed with 75 ml of methylbenzene
  8. customThe layers were separated
  9. extractionThe product was extracted with dichloromethane
  10. customthe extract was dried
  11. filtrationfiltered
  12. customevaporated
  13. additionby adding 3ml of a mixture of hydrochloric acid in 2-propanol (4.8N)
  14. stirringAfter stirring for 2 hours the product
  15. filtrationwas filtered off
  16. washwashed with 2-propanol
  17. customdried in vacuo at 50° C.

출처 및 근거

ORD 기록
ord-b323c2d887a741c9975abf1542688a09
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05746840

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