Dichloromethane → 4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methane-sulfonylmethyl)phenyl]piperazine-1-carbothioic acid N-methylamide

HRID 25227

반응식

HRID 25227 반응식
ClCCl.[CH3:4][N:5]=[C:6]=[S:7].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[N:16]2[CH2:19][C:18](=[CH:20][S:21]([CH2:24][C:25]3[CH:26]=[C:27]([N:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)[CH:28]=[CH:29][CH:30]=3)(=[O:23])=[O:22])[CH2:17]2)=[CH:11][CH:10]=1>O>[CH3:4][NH:5][C:6]([N:34]1[CH2:35][CH2:36][N:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][S:21]([CH:20]=[C:18]3[CH2:17][N:16]([CH:15]([C:12]4[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=4)[C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)[CH2:19]3)(=[O:22])=[O:23])[CH:26]=2)[CH2:32][CH2:33]1)=[S:7]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 11167Methyl isothiocyanateHCID 696356951-[3-({1-[Bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine

생성물 1

HCID 865847424-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methane-sulfonylmethyl)phenyl]piperazine-1-carbothioic acid N-methylamide수율 99.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

2 cm3 of dichloromethane and then 11 mg of methyl isothiocyanate are successively added, at a temperature close to 20° C., to 54.25 mg of 1-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine. After stirring for 6 hours at a temperature close to 20° C., 0.05 cm3 of water is added to the reaction mixture. After stirring for 15 minutes at the same temperature, the reaction medium is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (1 kPa) at a temperature close to 40° C. 61 mg of 4-[3-({1-[bis-(4-chlorophenyl)methyl]azetidin-3-ylidene}methanesulfonylmethyl)phenyl]piperazine-1-carbothioic acid N-methylamide are thus obtained in the form of a beige lacquer [1H NMR spectrum (400 MHz, CDCl3), δ in ppm): 2.77 (s, 3H), 3.20 (d, J=5 Hz, 3H), 3.32 (t, J=5.5 Hz, 4H), 3.81 (mt, 2H), 4.00 (t, J=5.5 Hz, 4H), 4.33 (mt, 2H), 4.49 (s, 1H), 5.63 (broad q, J=5 Hz, 1H), 6.80 (d, J=8 Hz, 1H), 6.85 (dd, J=8 and 2.5 Hz, 1H), 6.94 (broad s, 1H), from 7.20 to 7.30 (mt, 5H), 7.32 (d, J=8 Hz, 4H)].

후처리

  1. customclose to 20° C.
  2. stirringAfter stirring for 15 minutes at the same temperature
  3. dry with materialthe reaction medium is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (1 kPa) at a temperature
  6. customclose to 40° C

출처 및 근거

ORD 기록
ord-4cb1fbf1270f4094a228ba777ebc40c0
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858603B2

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