Sodium Azide → Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

HRID 494700노트

반응식

HRID 494700 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7](=[O:25])[C:8]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:11](Cl)=[N:10][CH:9]=1>CN(C=O)C.O>[CH3:5][O:6][C:7](=[O:25])[C:8]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[Cl:22])=[C:12]([Cl:23])[C:11]([N:1]=[N+:2]=[N-:3])=[N:10][CH:9]=1

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 11603943Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinate

생성물 1

HCID 59519382Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Sodium azide (4.4 g, 68 mmol) was added to a suspension of 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid methyl ester (26) (13.89 g, 33.8 mmol) in DMF (200 mL) and the mixture allowed to stir at room temperature overnight. The solution was diluted with water (600 mL) and the resulting white precipitate was collected by filtration and washed with water. The solids were dissolved into THF. Two volumes of diethyl ether were added and the organic solution washed with brine, dried over NaSO4, filtered, and concentrated in vacuo to the desired product (27) as a light yellow solid (12.94 g, 92%).

후처리

  1. filtrationthe resulting white precipitate was collected by filtration
  2. washwashed with water
  3. dissolutionThe solids were dissolved into THF
  4. additionTwo volumes of diethyl ether were added
  5. washthe organic solution washed with brine
  6. dry with materialdried over NaSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to the desired product (27) as a light yellow solid (12.94 g, 92%)

출처 및 근거

ORD 기록
ord-85f60a9474a742ee938e2975590010d8
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538120B2

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