Benzoic anhydride → HCID 17961693, compound

HRID 1161892Notes

Reaction equation

HRID 1161892 reaction equation
O[N:2]([C:4](=[NH:24])[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH3:3].CO[C:27]([C:29]#[C:30][C:31]([O:33][CH3:34])=[O:32])=[O:28].[O:35](C(C1C=CC=CC=1)=O)[C:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:37]>C(Cl)(Cl)Cl>[C:36]([O:37][C:29]1[C:27](=[O:28])[N:2]([CH3:3])[C:4]([CH:5]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]2[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[N:24][C:30]=1[C:31]([O:33][CH3:34])=[O:32])(=[O:35])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 7167Benzoic anhydrideHCID 12980Dimethyl acetylenedicarboxylateHCID 17961828HCID 17961828, compound

Product 1

HCID 17961693HCID 17961693, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
160 °C

Procedure

The product of Step 1 was dissolved in CHCl3 and dimethylacetylenedicarboxylate was added dropwise (1.2 eq.) at room temperature. After 4 h the mixture was evaporated, and the residue was dissolved in xylene and stirred at 160° C. for 2 days. The solvent was then evaporated, and the residue was dissolved in pyridine, after which (PhCO)2O (2 eq.) was added and the reaction mixture was stirred for 2 days. After evaporation, the resulting crude oil was diluted with EtOAc, washed with HCl 1N, dried over Na2SO4 and evaporated. The product was purified by flash chromatography on silica gel (EtOAc/petroleum ether, 1:4) to afford the title product.

Workup

  1. customAfter 4 h the mixture was evaporated
  2. dissolutionthe residue was dissolved in xylene
  3. customThe solvent was then evaporated
  4. dissolutionthe residue was dissolved in pyridine
  5. stirringthe reaction mixture was stirred for 2 days
  6. customAfter evaporation
  7. additionthe resulting crude oil was diluted with EtOAc
  8. washwashed with HCl 1N
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. customThe product was purified by flash chromatography on silica gel (EtOAc/petroleum ether, 1:4)

Sources & evidence

ORD record
ord-db5ff95da66a4b829858d4a039d67c57
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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