Nitrogen → Diethyl 4-(morpholinosulfonyl)benzylphosphonate

HRID 244271노트

반응식

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[P:18]([O:25]CC)([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21].N#N>>[O:15]1[CH2:16][CH2:17][N:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:13][CH2:14]1

참가 물질

반응물 3

HCID 947Nitrogen

HCID 31215Triethyl phosphite

HCID 27796804-((4-(Bromomethyl)phenyl)sulfonyl)morpholine

생성물 1

HCID 86654283Diethyl 4-(morpholinosulfonyl)benzylphosphonate수율 71.3%

반응 조건

온도: 100 °C

실험 절차

The aforementioned compound 1, (500 mg, 1.56 mmol) and triethyl phosphite (1.07 mL, 6.24 mmol) was mixed and heated to 100° C. for 1 hr. The reaction mixture was subjected to N2 flow over weekend to remove the excess ethyl phosphite. The resulting yellow oil was purified on a 12 g silica gel column to yield a colorless oil (420 mg, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.72 (d, J=8.4 Hz, 2H), 7.54 (dd, J1=8.4 Hz, J2=2.4 Hz, 2H), 4.1-4.0 (m, 4H), 3.77-3.72 (m, 4H), 3.25 (d, J=22.4 Hz, 2H), 3.02-2.96 (m, 4H), 1.27 (t, J=7.2 Hz, 6H).

후처리

customto remove the excess ethyl phosphite
customThe resulting yellow oil was purified on a 12 g silica gel column

출처 및 근거

ORD 기록: ord-6e85b435c5a64fb7bb822cbf0f8f5ee2
출처 데이터셋: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08658129B2

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