Chloroacetyl chloride → 2-Chloro-1-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanone

HRID 424517Notes

Reaction equation

HRID 424517 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[N+:6]([C:9]1[CH:10]=[CH:11][C:12]2[NH:17][CH2:16][CH2:15][S:14][C:13]=2[CH:18]=1)([O-:8])=[O:7]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:17]1[CH2:16][CH2:15][S:14][C:13]2[CH:18]=[C:9]([N+:6]([O-:8])=[O:7])[CH:10]=[CH:11][C:12]1=2)=[O:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 204961217-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

Product 1

HCID 591440782-Chloro-1-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

2-Chloroacetyl chloride (4.08 mL, 50.9 mmol) was added dropwise to a solution containing 7-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine (5 g, 25.5 mmol) in toluene (30 mL). The mixture was refluxed at 110° C. for 20 minutes. The mixture was quenched with saturated sodium bicarbonate solution (100 mL). The mixture was transferred to a separatory funnel and extracted with EtOAc (4×100 mL). The crude material was filtered through a pad of silica gel and washed with EtOAc. The filtrate was concentrated to give a yellow-brown solid. 1H-NMR (DMSO-d6) δ 8.12 (d, J=2.7 Hz, 1H), 7.94 (dd, J=2.7, 9.0 Hz, 1H), 7.72 (d, J=9.0 Hz, 1H), 4.63 (s, 2H), 3.96 (t, J=5.1 Hz, 2H), 3.32 (t, J=5.4 Hz, 2H, overlap with solvent peak); ESI-MS (m/z, %): 273 (MH+, 100), 295 (40).

Workup

  1. customThe mixture was quenched with saturated sodium bicarbonate solution (100 mL)
  2. customThe mixture was transferred to a separatory funnel
  3. extractionextracted with EtOAc (4×100 mL)
  4. filtrationThe crude material was filtered through a pad of silica gel
  5. washwashed with EtOAc
  6. concentrationThe filtrate was concentrated
  7. customto give a yellow-brown solid

Sources & evidence

ORD record
ord-0db6c6b1c1194f86950376e6783438eb
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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