Dimethylformamide → HCID 18617480, compound

HRID 1264214Notes

Reaction equation

HRID 1264214 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])([CH3:16])[C:13](O)=[O:14])=[CH:8][CH:7]=1.C[N:19](C=O)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])([CH3:16])[C:13]([NH2:19])=[O:14])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 18182605HCID 18182605, compound

Product 1

HCID 18617480HCID 18617480, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(furan-2-yl)-phenyl)-2-methyl-propionic Acid (reference example 28) (115 mg, 0.5 mmol) in CH2Cl2 (3 mL) is added DMF (10 mL) followed by oxalyl chloride (0.3 mL, 2M in CH2Cl2). The resulting solution is stirred for 2.5 hours then concentrated. The residue is taken up in methanolic ammonia (7N) and stirred for 14.5 hours, then concentrated to give 124 mg of the title compound as a tan solid. 1H NMR (CDCl3) d 1.58 (s, 6H), 5.2 (bs, 1H), 5.3 (bs, 1H), 6.45 (dd, J=3, 1 Hz, 1H), 6.63 (m, 1H), 7.39 (m, 2H), 7.45 (bs, 1H), 7.65 (m, 2H). MS (EI), m/z 229 (M+).

Workup

  1. concentrationthen concentrated
  2. stirringstirred for 14.5 hours
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b60d892547674fd7aab5e931bcdf93f0
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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