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Phthalic Anhydride → HCID 69872359, compound

HRID 1007309
Notes
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Reaction equation

HRID 1007309 reaction equation
Cl.NO.C([N:6](CC)CC)C.[C:11]1([C:17]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:18]2[CH:22]=[C:21]([CH:23]3[CH2:25][CH:24]3[CH:26]=O)[N:20]=[CH:19]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(=O)OC(=O)C2=CC=CC=C12>C(#N)C>[C:11]1([C:17]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:18]2[CH:22]=[C:21]([C@@H:23]3[CH2:25][C@H:24]3[C:26]#[N:6])[N:20]=[CH:19]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 22669348HCID 22669348, compound

Product 1

HCID 69872359HCID 69872359, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

To a solution of hydroxylamine hydrochloride (816 mg, 12 mmol) in anhydrous acetonitrile (35 mL), were added triethylamine (1.6 ml, 12 mmol), and 2-[1-(triphenylmethyl)imidazol-4-yl]cyclopropanecarbaldehyde (4.0 g, 11 mmol) The resulting mixture was stirred for about 2 hours followed by the addition of phthalic anhydride (1.6 g, 11 mmol) under nitrogen. Then the reaction mixture was heated under reflux for 8 hours, concentrated under reduced pressure, diluted with 5% aqueous ammonia (30 mL), and extracted with ethyl acetate (3×40 ml). The organic layer was dried with MgSO4, and then evaporated under reduced pressure. The resulting residue was purified on a silica gel column using ethyl acetate/hexane (v/v:1/6) as the eluting solvent to give the title compound as a pale yellow solid (2.4 g, 64% yield).

Workup

  1. temperatureThen the reaction mixture was heated
  2. temperatureunder reflux for 8 hours
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with 5% aqueous ammonia (30 mL)
  5. extractionextracted with ethyl acetate (3×40 ml)
  6. dry with materialThe organic layer was dried with MgSO4
  7. customevaporated under reduced pressure
  8. customThe resulting residue was purified on a silica gel column

Sources & evidence

ORD record
ord-ef0a4d42071f41449566183949312845
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06794405B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes