1,1'-Carbonyldiimidazole → HCID 18510213, compound

HRID 1371047Notes

Reaction equation

HRID 1371047 reaction equation
CO[C:3]([O:20]C)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[NH:35][C:36](=[NH:38])[CH3:37]>CN(C=O)C.O>[CH3:37][C:36]1[N:38]=[C:9]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:20])=[CH:13][CH:12]=2)[O:11][N:35]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 18510240HCID 18510240, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 18510213HCID 18510213, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 4-(2,2-dimethoxy-2-phenylethyl)benzoic acid (1.1 g, 3.84 mmole) in DMF (15 mL) was added carbonyldiimidazole (0.68 g, 4.2 mmole). After 20 min, N-hydroxy ethanimidamide (0.33 g, 4.5 mmole) was added and the mixture stirred for 45 min. at r.t. followed by 100° C. overnight. The reaction was cooled, poured in H2O (30 mL) and extracted with hexane/ethylacetate 1:1. The organic phase was dried over Na2SO4 and concentrated. The residue was dissolved in 100 mL acetone and treated with p-toluene sulfonic acid (100 mg) for 2 h. Et3N (0.5 mL) was added, and the mixture was concentrated to dryness. The residue was dissolved in 2:1 hexane/ethyl acetate (10 mL) and passed through a pad of silica gel, eluting with 1: 1 hexane:EtOAc. The fractions were concentrated, and the residue was stirred with 4:1 hexane:EtOAc 10 mL to give 0.49 g of the desired compound.

Workup

  1. waitfollowed by 100° C. overnight
  2. temperatureThe reaction was cooled
  3. extractionextracted with hexane/ethylacetate 1:1
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 100 mL acetone
  7. additiontreated with p-toluene sulfonic acid (100 mg) for 2 h
  8. additionEt3N (0.5 mL) was added
  9. concentrationthe mixture was concentrated to dryness
  10. dissolutionThe residue was dissolved in 2:1 hexane/ethyl acetate (10 mL)
  11. washeluting with 1: 1 hexane
  12. concentrationThe fractions were concentrated
  13. stirringthe residue was stirred with 4:1 hexane

Sources & evidence

ORD record
ord-03c872a2369842f9a979201cd07b3128
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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