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

HRID 558209ノート

反応式

HRID 558209 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 59519382Methyl 6-azido-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bd574c8eff904602aa4f8ee50bea8ed6
出典データセット
uspto-grants-2011_11
特許番号
US08063049B2

反応ノート

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