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Dimethylformamide → 4Iodo-benzoic acid N'-(2,2-dimethyl-propionyl)-hydrazide

HRID 31409
ノート
印刷プレビュー

反応式

HRID 31409 の反応式
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(O[C:16]([CH3:19])([CH3:18])[CH3:17])(=O)NN.C[N:21](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.C[N:64](C)[CH:65]=[O:66]>>[CH3:17][C:16]([CH3:19])([CH3:18])[C:65]([NH:64][NH:21][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:10][CH:9]=1)=[O:66]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 6

HCID 6228DimethylformamideHCID 120854-Iodobenzoic acidHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 693159064Iodo-benzoic acid N'-(2,2-dimethyl-propionyl)-hydrazide

実験手順

4-Iodobenzoic acid (5 g, 20.2 mmol) was dissolved in dimethylformamide (50 ml). To this was added tert-butyl carbazate (2.66 g, 20.2 mmol), HATU (9.2 g, 24.2 mmol), 1-hydroxybenzotriazole (2.7 g, 20.2 mmol) and N,N-diisopropylethylamine (10.5 ml, 60.5 mmol). The mixture was stirred for 17 hours at room temperature. The solvent was removed in vacuo and the residue partitioned between dichloromethane (75 ml) and saturated aqueous sodium bicarbonate solution (75 ml). The organic layer was washed with water (100 ml), brine (100 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. The desired product was obtained as a cream solid (4.6 g, 12.7 mmol).

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between dichloromethane (75 ml) and saturated aqueous sodium bicarbonate solution (75 ml)
  3. washThe organic layer was washed with water (100 ml), brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-42cdd1f4f85041759000fb71106a03b8
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07425555B2

反応ノート

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