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

HRID 424534ノート

反応式

HRID 424534 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7791ed4bc1074953a561bff8b2208dd8
出典データセット
uspto-grants-2012_01
特許番号
US08106043B2

反応ノート

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