N-ethyl-N-(oxan-4-yl)carbamoyl chloride → N-ethyl-N-(tetrahydro-2H-pyran-4-yl)-4-(2-chlorophenyl)-4,5-dihydro-1H-tetrazol-5-one-1-carboxamide

HRID 650866노트

반응식

HRID 650866 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[N:11]=[N:10][NH:9]1.[CH2:14]([N:16]([CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:17](Cl)=[O:18])[CH3:15]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH2:14]([N:16]([CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:17]([N:11]1[C:12](=[O:13])[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:9]=[N:10]1)=[O:18])[CH3:15]

참가 물질

5

반응물 2

HCID 11127103N-ethyl-N-(oxan-4-yl)carbamoyl chlorideHCID 178518972HCID 178518972, 화합물

생성물 1

HCID 11013583N-ethyl-N-(tetrahydro-2H-pyran-4-yl)-4-(2-chlorophenyl)-4,5-dihydro-1H-tetrazol-5-one-1-carboxamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매

실험 절차

3.7 g (19 mmol) of 1-(2-chlorophenyl)-1,2-dihydro-5H-tetrazol-5-one, 3.6 g (19 mmol) of N-ethyl-N-(tetrahydro-2H-pyran-4-yl)carbamoyl chloride and 2.6 g (21 mmol) of 4-dimethylaminopyridine in 150 ml of toluene were heated under reflux for 5 hours. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (eluent hexane/ethyl acetate 2:1). Yield 5.5 g. 1H NMR (270 MHz, in CDCl3): δ=1.20-1.40 (m, 3H), 1.80-2.05 (m, 4H), 3.30-3.60 (m, 4H), 3.70-4.50 (m, 3H), 7.40-7.60 (m, 4H).

후처리

  1. temperatureunder reflux for 5 hours
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent hexane/ethyl acetate 2:1)

출처 및 근거

ORD 기록
ord-f4e2ad08a4a94f6a8acac5d84d95d13b
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06277790B1

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