Hydrochloric Acid → HCID 178485344、化合物

HRID 448908ノート

反応式

HRID 448908 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[C:5]([N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]#[N:20])[CH3:8])=[O:6].[N:25]([Sn](CCCC)(CCCC)CCCC)=[N+:26]=[N-:27].C([Al](CC)CC)C.Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[C:5]([N:7]([CH3:8])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]1[NH:27][N:26]=[N:25][N:20]=1)=[O:6]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 16682930TriethylaluminumHCID 686031543-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide

生成物 1

HCID 178485344HCID 178485344、化合物収率 87.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide (2.0 g, 4.9 mmol), azidotributyltin (4.03 mL, 14.7 mmol) and triethylaluminum (7.74 mL, 14.7 mmol, 25% in toluene) in toluene (25 mL) was heated at 80° C. for 5 hrs. The mixture was allowed to cool to room temperature and was acidified with 1N HCl. The mixture was extracted with DCM. The organic layer was washed with water and brine, and was dried. The filtrate was concentrated in vacuo and the residue purified by silica gel column chromatography (eluent: 3% MeOH in DCM) to afford 3-bromo-4-chloro-N-methyl-N-{2-[3-(1H-tetrazol-5-yl)-propoxy]-phenyl}-benzamide (1.93 g). MS [M+H]+: 451.9; tR=2.26 min. (method 1)

後処理

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with DCM
  3. washThe organic layer was washed with water and brine
  4. customwas dried
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue purified by silica gel column chromatography (eluent: 3% MeOH in DCM)

出典と根拠

ORDレコード
ord-fcaeb249d08e45788511178bc49fc0a1
出典データセット
uspto-grants-2013_07
特許番号
US08481738B2

反応ノート

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