Dimethylformamide → HCID 11073620, compound

HRID 1007049Notes

Reaction equation

HRID 1007049 reaction equation
O=P(Cl)(Cl)Cl.CN([CH:9]=[O:10])C.[CH2:11]1[CH2:19][O:18][C:17]2[C:13](=[CH:14][NH:15][CH:16]=2)[O:12]1.[OH-].[Na+]>C(Cl)Cl>[CH:9]([C:14]1[NH:15][CH:16]=[C:17]2[O:18][CH2:19][CH2:11][O:12][C:13]=12)=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 162178522,3-Dihydro-6H-[1,4]dioxino[2,3-c]pyrrole

Product 1

HCID 11073620HCID 11073620, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

POCl3 (1.67 g, 10.92 mmol) was added to a solution of DMF (0.84 g, 11.44 mmol) in methylene chloride (5.0 mL) at 0° C. and the reaction mixture allowed to come to room temperature. The reaction mixture was then slowly added to a solution of 3,4-ethylenedioxypyrrole (1.3 g, 10.40 mmol) in methylene chloride (5.0 mL) at 0° C. and allowed to come to room temperature. After stirring for 12 h, an excess of 3.0 M NaOH solution was added and stirred for 2 h in a hot water bath. The reaction mixture was extracted with methylene chloride (40 mL×3) and the combined organic layers were dried over MgSO4. Purification of the residue was accomplished by chromatography on silica gel using hexane/ethyl acetate (2:1) as eluent to afford the product as a white solid (1.5 g, 65%): mp 147° C.; 1H NMR (300 MHz, CDCl3) δ9.43 (s, 1H), 9.02 (br, 1H), 6.62 (d, J=3.8 Hz, 1H), 4.24 (m, 4H); Anal. Calcd for C7H7NO3: C, 54.90; H, 4.61; N, 9.15. Found: C, 55.03; H, 4.48; N, 9.14.

Workup

  1. customto come to room temperature
  2. customto come to room temperature
  3. stirringstirred for 2 h in a hot water bath
  4. extractionThe reaction mixture was extracted with methylene chloride (40 mL×3)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. customPurification of the residue

Sources & evidence

ORD record
ord-d5b0c1278a784e8bb5b58b9c539dde6c
Source dataset
uspto-grants-2004_09
Patent number
US06791738B2

Reaction notes

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