Chloroacetyl chloride → 2-Chloro-1-(6-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanone

HRID 424554Notes

Reaction equation

HRID 424554 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[S:8][CH2:9][CH2:10][NH:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].[Cl:14][CH2:15][C:16](Cl)=[O:17]>C1COCC1.C(OCC)(=O)C>[Cl:14][CH2:15][C:16]([N:11]1[CH2:10][CH2:9][S:8][C:7]2[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]1=2)=[O:17]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 457916016-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

Product 1

HCID 591441332-Chloro-1-(6-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanoneYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 6-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine (620 mg, 3.16 mmol) in THF (10 mL) was added 2-chloroacetyl chloride (0.277 mL, 3.48 mmol). The resulting mixture was then stirred at 60° C. for 10 minutes The mixture was then diluted with ethyl acetate and washed with water (3×), 1:1 water:saturated sodium carbonate, and brine. The organic phase was dried, filtered, and concentrated, giving the desired product (860 mg, 100%). 1H NMR (DMSO-d6) δ 8.36 (d, J=2.1 Hz, 1H), 7.96 (dd, J=8.7, 2.1 Hz, 1H), 7.52 (d, J=8.7 Hz, 1H), 4.63 (s, 2H), 3.99-3.92 (m, 2H), 3.39-3.33 (m, 2H); ESI-MS (m/z, %): 295 (M+Na, 68), 273 (MH+, 100), 197 (43).

Workup

  1. washwashed with water (3×), 1:1 water
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a92e1d28a2df4a07aad2fad560a9c4d8
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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