Hydrochloric Acid → 5-(3-nitrophenyl)tetrazole

HRID 440792

反応式

HRID 440792 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.C(N(CC)CC)C.[N-:20]=[N+:21]=[N-:22].[Na+].Cl>CN1CCCC1=O>[N+:9]([C:5]1[CH:4]=[C:3]([C:1]2[NH:22][N:21]=[N:20][N:2]=2)[CH:8]=[CH:7][CH:6]=1)([O-:11])=[O:10]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 120793-NitrobenzonitrileHCID 33557Sodium Azide

生成物 1

HCID 2851295-(3-nitrophenyl)tetrazole収率 88.9%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
160 °C

実験手順

To a solution of 3-cyanonitrobenzene-(20 g, 0.13 mol) in 1-methyl-2-pyrrolidinone (200 ml) was added triethylamine hydrochloride (27.9 g, 0.20 mol) followed by sodium azide (26.4 g, 0.40 mol). The mixture was heated at 160° C. for 1.5 h, then cooled to ambient temperature, poured into ice water (1000 ml) and acidified using 5M HCl. The solid which precipitated from the mixture was filtered, washed with water and dried under vacuum at 50° C. to afford the title tetrazole (22.1 g, 86%) as a beige powder; mp 154°-156° C; δH (360 MHz, CDCl3), 7.59 (1H, t, J=9 Hz), 8.19 (1H, d, J=8 Hz), 8.36 (1H, d, J=8 Hz), 8.86 (1H, s).

後処理

  1. temperaturecooled to ambient temperature
  2. customThe solid which precipitated from the mixture
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum at 50° C.

出典と根拠

ORDレコード
ord-3d319f418d134ab0a512648139f0bdff
出典データセット
uspto-grants-1996_05
特許番号
US05521175

関連ノート

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