Triethylamine → 2-(Diethoxyphosphinyloxymethyl)-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 1736307노트

반응식

HRID 1736307 반응식
Cl[CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][CH3:11])[N:5]([CH3:12])[S:4]1(=[O:14])=[O:13].[P:15]([O-:23])([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:18]([O:17][P:15]([O:20][CH2:21][CH3:22])([O:23][CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][CH3:11])[N:5]([CH3:12])[S:4]1(=[O:14])=[O:13])=[O:16])[CH3:19]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 5166299Diethyl phosphoric acidHCID 158374782-Chloromethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

생성물 1

HCID 99067832-(Diethoxyphosphinyloxymethyl)-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide수율 66%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매2회HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-chloromethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1 g; 4.16 mmol), diethyl phosphate (Formula III: A=B=Et) (0.96 g, 6.63 mmol), tetrabutylammonium bromide (94 mg, 0.29 mmol) and triethylamine (0.63 g, 6.23 mmol) in methylene chloride (20 ml) was allowed to reflux for 24 hours. After adding an additional tetrabutylammonium bromide, the mixture was refluxed for an additional 48 hours, and then cooled. The mixture was purified by silica gel flash chromatography (ethyl acetate/hexane) to afford 0.98 g (66%) of 2-(diethoxyphosphinyloxymethyl)-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: A=B=Et; R1 =H; R2 =propyl; R3 =CH3) as an oil.

후처리

  1. temperatureto reflux for 24 hours
  2. temperaturethe mixture was refluxed for an additional 48 hours
  3. temperaturecooled
  4. customThe mixture was purified by silica gel flash chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-3f7aadd1232a4512bf79a8cffa7c2554
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05541168

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