Hydrochloric Acid → 2-Tert-butyl-5-nitrobenzene-1-sulfonyl chloride

HRID 74075

反応式

HRID 74075 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1N)([CH3:4])([CH3:3])[CH3:2].N([O-])=O.[Na+].[O-:19][S:20]([O-:22])=O.[Na+].[Na+].[ClH:25]>O.[O-]S([O-])(=O)=O.[Cu+2]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[S:20]([Cl:25])(=[O:22])=[O:19])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric Acid2 回HCID 24437Sodium Sulfite2 回HCID 8261032-Tert-butyl-5-nitroanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 574702642-Tert-butyl-5-nitrobenzene-1-sulfonyl chloride収率 17%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 962Water溶媒3 回

反応条件

温度
7.5 °C

実験手順

A suspension of 2-tert-butyl-5-nitrobenzenamine (0.971 g, 5 mmol) in conc. HCl (5 mL) was cooled to 5-10° C. and a solution of NaNO2 (0.433 g, 6.3 mmol) in H2O (0.83 mL) was added dropwise. Stirring was continued for 0.5 h, after which the mixture was vacuum filtered. The filtrate was added, simultaneously with a solution of Na2SO3 (1.57 g, 12.4 mmol) in H2O (2.7 mL), to a stirred solution of CuSO4 (0.190 g, 0.76 mmol) and Na2SO3 (1.57 g, 12.4 mmol) in HCl (11.7 mL) and H2O (2.7 mL) at 3-5° C. Stirring was continued for 0.5 h and the resulting precipitate was filtered off, washed with water and dried to give 2-tert-butyl-5-nitrobenzene-1-sulfonyl chloride (0.235 g, 17%). 1H NMR (400 MHz, DMSO-d6) δ 9.13 (d, J=2.5 Hz, 1H), 8.36 (dd, J=8.9, 2.5 Hz, 1H), 7.88 (d, J=8.9 Hz, 1H), 1.59 (s, 9H).

後処理

  1. filtrationfiltered
  2. stirringStirring
  3. waitwas continued for 0.5 h
  4. filtrationthe resulting precipitate was filtered off
  5. washwashed with water
  6. customdried

出典と根拠

ORDレコード
ord-2e4511d4a9c04551b89c1886bcceef17
出典データセット
uspto-grants-2014_09
特許番号
US08829204B2

関連ノート

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