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Hydrochloric Acid → HCID 131720911, 화합물

HRID 355360
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HRID 355360 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:10]#[N:11])=[C:4]([Cl:19])[CH:3]=1.Cl.[N:21]([O-])=O.[Na+].C([O-])(=O)C.[Na+].[CH2:30]([O:32][C:33](=[O:40])[NH:34][C:35](=[O:39])[CH2:36][C:37]#[N:38])[CH3:31]>O.C(O)(=O)C>[CH2:30]([O:32][C:33](=[O:40])[NH:34][C:35](=[O:39])[C:36](=[N:21][NH:1][C:2]1[CH:3]=[C:4]([Cl:19])[C:5]([CH:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:10]#[N:11])=[C:6]([Cl:8])[CH:7]=1)[C:37]#[N:38])[CH3:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 23112N-CyanoacetylethylcarbamateHCID 517045Sodium AcetateHCID 15068435(4-Amino-2,6-dichlorophenyl)(4-chlorophenyl)acetonitrile2회HCID 23668193Sodium Nitrite

생성물 1

HCID 131720911HCID 131720911, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

To a stirred and cooled (5-10 degrees C) mixture of 15.2 parts of 4-amino-2,6-dichloro-α-(4-chlorophenyl)-benzeneacetonitrile (intermediate 2), 14.4 parts of concentrate hydrochloric acid and 125 parts of acetic acid is added dropwise, during a 30 minutes period, a solution of 3.5 parts of sodium nitrite in 15 parts of water at about 10 degrees C. Upon completion, the whole is stirred for 30 minutes and then 10 parts of sodium acetate and 7.8 parts of ethyl(2-cyanoacetyl)carbamate are added, during a period of 2 hours, at room temperature. The reaction mixture is poured into 500 parts of water. The product is filtered off, washed with water and dissolved in dichloromethane. The organic layer is dried, filtered and evaporated. The residue is purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated in vacuo. The residue is stirred in 2-propanol. The product is filtered off, washed with 2,2'-oxybispropane and dried, yielding ethyl[2-[[3,5-dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]hydrazono]-2-cyanoacetyl]carbamate (intermediate 3).

후처리

  1. temperaturecooled
  2. additionis added dropwise, during a 30 minutes period
  3. customat about 10 degrees C
  4. stirringUpon completion, the whole is stirred for 30 minutes
  5. filtrationThe product is filtered off
  6. washwashed with water
  7. dissolutiondissolved in dichloromethane
  8. customThe organic layer is dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is purified by column chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  13. customThe pure fractions are collected
  14. customthe eluent is evaporated in vacuo
  15. stirringThe residue is stirred in 2-propanol
  16. filtrationThe product is filtered off
  17. washwashed with 2,2'-oxybispropane
  18. customdried

출처 및 근거

ORD 기록
ord-0d95f4f2b70444fb9f1b10efe3ac07a5
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05830893

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