Triethylamine → N,N,1-trimethyl-1H-pyrazole-4-carboxamide

HRID 1802271ノート

反応式

HRID 1802271 の反応式
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3]1.[CH2:10]([N:12](CC)[CH2:13]C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.CNC>CN(C=O)C>[CH3:10][N:12]([CH3:13])[C:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:9]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 6431601-Methyl-1H-pyrazole-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

生成物 1

HCID 59551573N,N,1-trimethyl-1H-pyrazole-4-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Methyl-1H-pyrazole-4-carboxylic acid (1.0 g, 7.93 mmol) was combined with DMF (10.0 ml) to give a light yellow solution. Triethylamine (3.3 ml, 23.8 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (2.8 g, 8.72 mmol) were added. The reaction mixture was set under argon and stirred for 1 h at RT. Then dimethylamine hydrochloride (679 mg, 8.33 mmol) was added. The reaction mixture was stirred over night. The solvent was evaporated and the residue was absorbed on silica gel and chromatographed (amine silica gel cartridge, CH2Cl2). The resulting brown oil was dried at the HV over night. Yield: 1.16 g (96%); brown oil; MS: m/z=154.1 [M+H]+.

後処理

  1. customto give a light yellow solution
  2. stirringThe reaction mixture was stirred over night
  3. customThe solvent was evaporated
  4. customthe residue was absorbed on silica gel
  5. customchromatographed (amine silica gel cartridge, CH2Cl2)
  6. customThe resulting brown oil was dried at the HV over night

出典と根拠

ORDレコード
ord-7052bce9aa1e439ca487024c77df2979
出典データセット
uspto-grants-2013_01
特許番号
US08349824B2

反応ノート

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