肼(无水) → 4-amino-N-(cyclopentyloxy)-3-nitrobenzenesulfonamide

HRID 29154

反应方程式

HRID 29154 反应方程式
[CH:1]1([O:6][N:7]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.NN.[N+:20]([C:23]1[CH:29]=[C:28]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[CH:26][C:24]=1[NH2:25])([O-:22])=[O:21].C(N(CC)C(C)C)(C)C>O1CCCC1.OS([O-])(=O)=O.[Na+].ClCCl>[NH2:25][C:24]1[CH:26]=[CH:27][C:28]([S:30]([NH:7][O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)(=[O:32])=[O:31])=[CH:29][C:23]=1[N+:20]([O-:22])=[O:21]

参与物

8

反应物 4

HCID 9321肼(无水)HCID 81531N,N-二异丙基乙胺HCID 102632872-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dioneHCID 129630684-Amino-3-nitrobenzene-1-sulfonyl chloride

产物 1

HCID 229971904-amino-N-(cyclopentyloxy)-3-nitrobenzenesulfonamide收率 68.1%

试剂、催化剂与溶剂 3

HCID 6344二氯甲烷溶剂HCID 8028四氢呋喃溶剂HCID 516919硫酸氢钠溶剂

实验过程

A solution of 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione (10.00 g, 43.30 mmol) in anhydrous tetrahydrofuran (100 mL) at ambient temperature under an Argon atmosphere was treated with anhydrous hydrazine (1.49 mL, 47.63 mmol). After stirring vigorously for 2.5 hours, the resulting slurry was filtered and washed with approximately 20 mL of anhydrous tetrahydrofuran. The filtrate was combined with o-nitroaniline-p-sulfonyl chloride (11.26 g, 47.63 mmol) and N,N-diisopropylethylamine (9.05 mL, 51.96 mmol) and stirred under an Argon atmosphere for 16 hrs. at ambient temperature. The reaction mixture was diluted with 1N NaHSO4 and dichloromethane and transferred to a separatory funnel. The organic phase was separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed with 5% aqueous potassium carbonate, dried over anhydrous magnesium sulfate, filtered through a pad of diatomaceous earth and evaporated in vacuo. The residue was purified on flash grade silica gel eluting with 1:1 ethyl acetate:hexane. Fractions containing the product were combined, evaporated in vacuo to a residue and triturated with hexane. The slurry was filtered and the product was dried under high vacuum to provide 4-amino-N-(cyclopentyloxy)-3-nitrobenzenesulfonamide (8.89 g, 68%) as a yellow solid. H1-NMR (chloroform-D3): 1.57 (m, 4H), 1.74 (m, 4H), 4.61 (m, 1H), 6.52 (b, 2H), 6.73 (s, H), 6.90 (d, 1H), 7.79 (m, 1H), 8.70 (d, 1H). MS(ESI): 324 (M+Na).

后处理

  1. filtrationthe resulting slurry was filtered
  2. washwashed with approximately 20 mL of anhydrous tetrahydrofuran
  3. stirringstirred under an Argon atmosphere for 16 hrs
  4. customat ambient temperature
  5. customtransferred to a separatory funnel
  6. customThe organic phase was separated
  7. extractionthe aqueous layer was extracted twice with dichloromethane
  8. washThe combined organic layers were washed with 5% aqueous potassium carbonate
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered through a pad of diatomaceous earth
  11. customevaporated in vacuo
  12. customThe residue was purified on flash grade silica gel eluting with 1:1 ethyl acetate
  13. additionFractions containing the product
  14. customevaporated in vacuo to a residue
  15. customtriturated with hexane
  16. filtrationThe slurry was filtered
  17. customthe product was dried under high vacuum

来源与证据

ORD记录
ord-92e5a1e073754054b06fe476538e78e5
来源数据集
uspto-grants-2008_09
专利号
US07419967B2

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