Triethylamine → N,N-diethyl-3-(N',N'-diethylthiocarbamoyloxy)picolinamide

HRID 52130

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HRID 52130 반응식
[OH:1][C:2]1[C:3]([C:8]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.CN1C(=O)N(C)CCC1.C(N(CC)CC)C.[CH2:31]([N:33]([CH2:37][CH3:38])[C:34](Cl)=[S:35])[CH3:32]>O>[CH2:11]([N:10]([CH2:13][CH3:14])[C:8](=[O:9])[C:3]1[C:2]([O:1][C:34](=[S:35])[N:33]([CH2:37][CH3:38])[CH2:31][CH3:32])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:12]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 66607Diethylthiocarbamoyl chlorideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 3020810N,N-diethyl-3-hydroxypyridine-2-carboxamide

생성물 1

HCID 19963243N,N-diethyl-3-(N',N'-diethylthiocarbamoyloxy)picolinamide수율 83%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

258.3 g (1.33 mol) of 3-hydroxy-N,N-diethylpicolinamide are introduced into 1 l of dimethylpropyleneurea and 213.2 ml (1.53 mol) of triethylamine at 0° C., and 222 g (1.464 mol) of diethylthiocarbamoyl chloride are introduced in the form of a solid. After the reaction mixture has been stirred for 2 hours at 0° C., it is poured into 2 l of water and extracted three times using ethyl acetate, the ethyl acetate phases are washed five times using 500 ml of water in each case, and the combined organic phases are dried over Na2SO4 and concentrated in vacuo at 60° C. Recrystallization from Et2O/hexane gives 341 g (83%) of brown crystals, m.p. 70°-72° C.

후처리

  1. extractionextracted three times
  2. washthe ethyl acetate phases are washed five times
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. concentrationconcentrated in vacuo at 60° C
  5. customRecrystallization from Et2O/hexane

출처 및 근거

ORD 기록
ord-7f4daed40d314eedb8125aa00e940a83
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616590

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