Dimethylformamide → HCID 22063969, compound

HRID 1828212Notes

Reaction equation

HRID 1828212 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].CN([CH:17]=[O:18])C.C(Cl)(=O)C(Cl)=O.[CH2:25]([N:27](CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:27]([O:18][CH3:17])[CH3:25])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 22063969HCID 22063969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Fluoro-3-nitrobenzoic acid (100 gm, 0.54 mol) was taken up in dry methylene chloride (1 L) and 1.5 mL of DMF was added. To this solution was added oxalyl chloride (61 mL, 0.702 mol). After 1.5 hours, the solvent was removed in vacuo and the crude acid chloride (yellow oil) was taken up in methylene chloride (50 mL) and slowly added to a stirring mixture of triethylamine (150.5 mL, 1.08 mol) and Weinreb amine hydrochloride (68.5 gm, 0.702 mol) in methylene chloride (950 mL) at 0 deg C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was washed with saturated sodium dihydrogen phosphate, followed by water. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo to an orange-yellow oil. The crude oil was triturated with pentane to give 110.28 gm (90%) of a yellow to off white powder.

Workup

  1. customthe solvent was removed in vacuo
  2. washThe reaction mixture was washed with saturated sodium dihydrogen phosphate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo to an orange-yellow oil
  5. customThe crude oil was triturated with pentane
  6. customto give 110.28 gm (90%) of a yellow to off white powder

Sources & evidence

ORD record
ord-1dfde700706e4c368ea573d0e01302a8
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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