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

HRID 558209노트

반응식

HRID 558209 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=[C:11](Cl)[C:10]=2[Cl:20])=[C:4]([Cl:21])[CH:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C.O>[N:22]([C:11]1[C:10]([Cl:20])=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[Cl:21])[C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1)=[N+:23]=[N-:24]

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-chloronicotinate수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Methyl 4-(4-bromo-2-chlorophenylamino)-5,6-dichloronicotinate (1.690 g, 4.14 mmol) was suspended in 30 ml DMF and the suspension was heated until everything went into solution. It was cooled down to room temperature and to that solution was added solid sodium azide (0.533 g, 8.2 mmol). The yellow solution was stirred for 17 h at room temperature and was diluted with water. The precipitate was filtered, washed with water and hexanes and dried in oil-pump vacuo at 50° C. for 2 h to obtain the title compound as a light-brown solid (1.5422 g, 90%). 1H-NMR (300 MHz, DMSO-D6): δ=9.85 (s, 1H), 8.90 (s, 1H), 7.80-7.79 (d, 1H), 7.46-7.40 (dd, 1H), 6.95-6.90 (d, 1H), 3.80 (s, 3H).

후처리

  1. temperaturethe suspension was heated until everything
  2. filtrationThe precipitate was filtered
  3. washwashed with water and hexanes
  4. customdried in oil-pump vacuo at 50° C. for 2 h

출처 및 근거

ORD 기록
ord-bd574c8eff904602aa4f8ee50bea8ed6
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063049B2

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