Citric Acid → HCID 66992743, compound

HRID 1855671Notes

Reaction equation

HRID 1855671 reaction equation
C1CCN2C(=NCCC2)CC1.[C:12]([N:31]1[CH:35]=[C:34]([CH:36]=O)[N:33]=[CH:32]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Br-].[O:39]=[C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42](=[O:49])[N:41]1[CH2:50][CH2:51][CH2:52][CH2:53][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[C:12]([N:31]1[CH:35]=[C:34]([CH:36]=[CH:53][CH2:52][CH2:51][CH2:50][N:41]2[C:42](=[O:49])[C:43]3[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:40]2=[O:39])[N:33]=[CH:32]1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 311Citric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 19914622[4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl](triphenyl)phosphanium bromide

Product 1

HCID 66992743HCID 66992743, compoundYield 51%

Procedure

0.663 ml (4.43 mmol) of DBU and 1.0 g (2.96 mmol) of 1-trityl-1H-imidazole-4-carbaldehyde are added to 2.41 g (4.43 mmol) of [4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)butyl]triphenylphosphonium bromide. The reaction medium is refluxed for 18 hours. The reaction is stopped by adding aqueous 5% citric acid solution and the organic compounds are extracted with CH2Cl2. The organic phase is dried over MgSO4, filtered and concentrated. The residue obtained is chromatographed on silica gel (eluent: heptane/EtOAc (6/4)). 785 mg of 2-[5-(1-trityl-1H-imidazol-4-yl)pent-4-enyl]isoindole-1,3-dione are obtained in a yield of 51%.

Workup

  1. temperatureThe reaction medium is refluxed for 18 hours
  2. extractionthe organic compounds are extracted with CH2Cl2
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customis chromatographed on silica gel (eluent: heptane/EtOAc (6/4))

Sources & evidence

ORD record
ord-41d02f3efbb04ea9b882a74e10d31bf3
Source dataset
uspto-grants-2015_02
Patent number
US08962846B2

Reaction notes

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