Cyclohexanol → Cyclohexyl 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylate

HRID 67263

반응식

HRID 67263 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11](=[O:15])[C:10]([C:16]([OH:18])=[O:17])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(O[CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=O.C1(O)CCCCC1>C1(C)C=CC=CC=1.CCCCCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11](=[O:15])[C:10]([C:16]([O:18][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:17])=[N:9]2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 7966CyclohexanolHCID 8471TriethylamineHCID 83262Carbonochloridic acid, cyclohexyl esterHCID 197225Fenridazon

생성물 1

HCID 13084122Cyclohexyl 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methylpyridazine-3-carboxylate수율 65%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매3회HCID 8058Hexane용매

실험 절차

To an ice cooled suspension of 5.29 g (0.02 mol) 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic Acid (see Example 12) and 2.02 g (0.02 mol) of triethylamine in 75 ml of toluene there is added 3.25 g (0.02 mol) of cyclohexyl chloroformate. The suspension formed is stirred at room temperature for 15 minutes and to it there is added 3.2 g (0.022 mol) of cyclohexanol in 50 ml of toluene. The mixture is stirred at room temperature for 38 hrs. and to it there is added 100 ml of water. The mixture is stirred at room temperature for 1 hr. and the toluene layer is isolated and poured into 600 ml of hexane. The suspension formed is stirred at room temperature for 1/2 hr. and is vacuum filtered. The filter cake is air dried to afford 4.5 g (65% yield) of product, mp 160°-162° C.

후처리

  1. customThe suspension formed
  2. stirringThe mixture is stirred at room temperature for 38 hrs
  3. stirringThe mixture is stirred at room temperature for 1 hr
  4. customThe suspension formed
  5. stirringis stirred at room temperature for 1/2 hr
  6. filtrationfiltered
  7. customdried

출처 및 근거

ORD 기록
ord-1ff062a96b93482eaad2b50dc2687f39
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04345934

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