Dimethylcarbamoyl Chloride → 4-[[(Diethylamino)methylene]amino]-3-pyridinol N,N-dimethyl carbamate

HRID 361336

反応式

HRID 361336 の反応式
[CH2:1]([N:3]([CH:6]=[N:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[OH:14])[CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C.O1CCCC1.[CH3:27][N:28]([CH3:32])[C:29](Cl)=[O:30]>CCOCC>[CH3:27][N:28]([CH3:32])[C:29]([O:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[N:7]=[CH:6][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:30]

参加物

6

反応物 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 15380930N,N-Diethyl-N'-(3-hydroxypyridin-4-yl)methanimidamide

生成物 1

HCID 677490774-[[(Diethylamino)methylene]amino]-3-pyridinol N,N-dimethyl carbamate収率 70.3%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution prepared from 4-[[(diethylamino)methylene]amino]-3-pyridinol (3.12 g), triethylamine (3.34 g) and tetrahydrofuran (50 mL) was added N,N-dimethylcarbamyl chloride (2.28 g) under nitrogen. The resulting mixture was stirred at ambient temperature for 6 hours, diluted with ether (50 mL) and filtered. The filtrate was concentrated under reduced pressure and the residue chromatographed on silica gel (elution with 10% methanol in dichloromethane) to give 3.00 g of solid. Recrystallization from ether/hexanes afforded 1.57 g of crystalline solid, m.p. 73°-74° C.

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue chromatographed on silica gel (elution with 10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-1a83521255a344ffad76d572f53ad5d2
出典データセット
uspto-grants-1999_02
特許番号
US05866565

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