Chloroacetyl chloride → HCID 14880548, compound

HRID 1917136Notes

Reaction equation

HRID 1917136 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:12][CH2:11][CH2:10][O:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].[Cl:14][CH2:15][C:16](Cl)=[O:17].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[Cl:14][CH2:15][C:16]([N:12]1[CH2:11][CH2:10][O:9][C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]1=2)=[O:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 184161517-Nitro-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 14880548HCID 14880548, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 7-nitro-3,4-dihydro-2H-benzo[b][1,4]oxazine (8 g, 44.4 mmol) in anhydrous toluene (100 mL) under positive argon pressure was treated dropwise with 2-chloroacetyl chloride (3.91 mL, 48.8 mmol). The mixture was heated at reflux for 25 minutes and became a bright yellow solution. The solution was allowed to cool to room temperature, and a saturated NaHCO3 solution (150 mL) was added. The mixture was transferred to a separatory funnel, and the product was extracted with CH2Cl2 (2×200 mL). The combined organic layers were filtered through a pad of silica gel, washed with CH2Cl2 (50 mL), and concentrated to give a yellow solid (10 g, 88%). 1H-NMR (DMSO-d6) δ 8.22 (d, J=9.0 Hz, 1H), 7.80 (dd, J=2.7, 9.3 Hz, 1H), 7.72 (d, J=2.7 Hz, 1H), 4.74 (s, 2H), 4.40 (t, J=4.2 Hz, 2H), 3.94 (t, J=4.8 Hz, 2H); ESI-MS (m/z, %): 279 (MNa+, 30), 257 (MH+, 100).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 25 minutes
  3. customThe mixture was transferred to a separatory funnel
  4. extractionthe product was extracted with CH2Cl2 (2×200 mL)
  5. filtrationThe combined organic layers were filtered through a pad of silica gel
  6. washwashed with CH2Cl2 (50 mL)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d9b3ffdfa09145cebb3c1e56957ad5dc
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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