1-Chloroethyl chloroformate → N-Methyl-2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanamine

HRID 424534노트

반응식

HRID 424534 반응식
ClC(OC(Cl)C)=O.[CH3:8][N:9](C)[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][S:15][C:14]2[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:13]1=2>ClCCCl>[CH3:8][NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][S:15][C:14]2[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:13]1=2

참가 물질

4

반응물 2

HCID 5213051-Chloroethyl chloroformateHCID 59144138N,N-Dimethyl-2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanamine

생성물 1

HCID 59144162N-Methyl-2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanamine

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

1-Chloroethyl chloroformate (0.612 mL, 5.61 mmol) was added to a solution of N,N-dimethyl-2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanamine (1.0 g, 3.74 mmol) in 1,2-dichloroethane (20 mL) at 0° C. in an argon atmosphere. The solution was brought to room temperature and refluxed under vigorous stirring for 3 hours. The solution was concentrated and then refluxed in MeOH (20 mL). The solution was concentrated to give dark brown viscous oil (1.05 g, quantitative). 1H NMR (CDCl3) δ 7.96 (d, J=2.4 Hz, 1H), 7.86 (dd, J=2.7, 9.3 Hz, 1H), 6.67 (d, J=9.3 Hz, 1H), 3.85-3.82 (m, 2H), 3.55 (t, J=6.9 Hz, 2H), 3.03-3.00 (m, 2H), 2.86 (t, J=6.9 Hz, 2H), 2.48 (s, 3H); ESI-MS (m/z, %): 256, 254 (MH+, 100).

후처리

  1. customwas brought to room temperature
  2. temperaturerefluxed
  3. concentrationThe solution was concentrated
  4. temperaturerefluxed in MeOH (20 mL)
  5. concentrationThe solution was concentrated
  6. customto give dark brown viscous oil (1.05 g, quantitative)

출처 및 근거

ORD 기록
ord-7791ed4bc1074953a561bff8b2208dd8
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106043B2

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