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

HRID 1917190Notes

Reaction equation

HRID 1917190 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-557d55cfee4048b0bbfa5f1d147fc967
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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