Ammonia → 2-(2-Hydroxyethylamino)-1-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanone

HRID 424518Notes

Reaction equation

HRID 424518 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][S:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]1=2)=[O:4].Cl.O1CCOCC1.[NH2:25][CH2:26][CH2:27][OH:28].N>C1COCC1.O.CCOC(C)=O.C(=O)(O)[O-].[Na+].CO.C(Cl)Cl>[OH:28][CH2:27][CH2:26][NH:25][CH2:2][C:3]([N:5]1[CH2:10][CH2:9][S:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]1=2)=[O:4]

Participants

12

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 700EthanolamineHCID 312751,4-DioxaneHCID 591440782-Chloro-1-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanone

Product 1

HCID 667044232-(2-Hydroxyethylamino)-1-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanoneYield 29.4%

Reagents, catalysts & solvents 6

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-chloro-1-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanone (1.0 g, 3.67 mmol) in THF (20 mL) was treated with 4M HCl in 1,4-dioxane (4.58 mL, 18.33 mmol), followed by the slow addition of a solution of 2-aminoethanol (2.207 mL, 36.7 mmol) in water (4 mL). The dark solution was stirred at room temperature for 24 hours. The mixture was diluted with EtOAc (50 mL) and saturated sodium bicarbonate (100 mL), then stirred for 20 minutes. The contents were poured into a separatory funnel, and the organic layer was separated, dried (Na2SO4), filtered, and concentrated to give a dark yellow residue. This residue was subjected to flash chromatography on silica gel using 5:95 MeOH:CH2Cl2 followed by 5:95 (2M NH3 in MeOH):CH2Cl2 to give a yellow residue (320 mg, 29.4%). 1H-NMR (CDCl3) δ 8.14 (d, J=2.7 Hz, 1H), 7.95 (dd, J=2.7, 9.0 Hz, 1H), 7.37 (d, J=9.0 Hz, 1H), 4.02 (t, J=5.1 Hz, 2H), 3.61 (t, J=5.1 Hz, 2H), 3.57 (s, 2H), 3.28 (t, J=5.4 Hz, 2H), 2.77 (t, J=4.8 Hz, 2H); ESI-MS (m/z, %): 298 (MH+, 100%).

Workup

  1. stirringstirred for 20 minutes
  2. additionThe contents were poured into a separatory funnel
  3. customthe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a dark yellow residue

Sources & evidence

ORD record
ord-b32695011aca42d6a0c8ec9a8042ba49
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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