Methanol → 4-[[(Diisopropylamino)methylene]amino]-3-pyridinol N,N-dimethyl carbamate

HRID 362217

反応式

HRID 362217 の反応式
[CH:1]([N:4]([CH:8]=[N:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[OH:16])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27].CO>CCOCC.C(Cl)Cl>[CH3:24][N:25]([CH3:29])[C:26]([O:16][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:10]=1[N:9]=[CH:8][N:4]([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:2])[CH3:3])=[O:27]

参加物

7

反応物 4

HCID 887MethanolHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 153809314-[[(Diisopropylamino)methylene]amino]-3-pyridinol

生成物 1

HCID 677490834-[[(Diisopropylamino)methylene]amino]-3-pyridinol N,N-dimethyl carbamate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

To a stirred mixture of 4-[[(diisopropylamino)methylene]amino]-3-pyridinol (1.06 g) and triethylamine (1.0 ml) in 25 ml dry Et2O was added dimethyl carbamyl chloride (0.53 ml). The mixture was stirred at room temperature for 2 hours, after which no starting material remained as seen by TLC (silica, 10:90 CH3OH:CH2Cl2). The mixture was diluted with 25 ml Et2O, filtered, washed with Et2O, and the filtrate concentrated in vacuo and chromatography on silica using EtOAc eluent. The fractions containing desired product were combined and concentrated to provide 500 mg of pure product. Another run was carried out in the same manner as above using 740 mg of starting material. The products from both runs were combined. Recrystallization attempts failed, and the product was dried in vacuo to provide 790 mg of a white solid, m.p. 76°-79° C.

後処理

  1. filtrationfiltered
  2. washwashed with Et2O
  3. concentrationthe filtrate concentrated in vacuo and chromatography on silica
  4. additionThe fractions containing desired product
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-55b4507bc77f454c88f27ac3dfb2534f
出典データセット
uspto-grants-1999_02
特許番号
US05869480

関連ノート

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