Benzene → HCID 19772346, compound

HRID 1463535Notes

Reaction equation

HRID 1463535 reaction equation
[C:1]1([C:7]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][S:9][C:8]=2C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])=CC=1.C1C=CC=CC=1.Cl.[C:44]([O:47][C:48]1[C:54]([CH3:55])=[CH:53][C:51]([NH2:52])=[CH:50][C:49]=1[CH3:56])(=[O:46])[CH3:45].C([N:59]([CH2:62]C)CC)C>>[C:44]([O:47][C:48]1[C:54]([CH3:55])=[CH:53][C:51]([NH:52][C:62]([NH:59][C:8]2[S:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:27])=[CH:50][C:49]=1[CH3:56])(=[O:46])[CH3:45]

Participants

6

Reactant 5

HCID 241BenzeneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19090525HCID 19090525, compoundHCID 19090551HCID 19090551, compound

Product 1

HCID 19772346HCID 19772346, compound

Procedure

To a mixture of 4-phenyl-1H-2-benzothiopyran-3-carboxylic acid (in Reference Example 13) (268 mg), DPPA (330 mg) and benzene (5 ml) was added dropwise to triethylamime (0.14 ml) and the mixture was stirred at room temperature for 30 minutes, then refluxed for 30 minutes. To the mixture were added 4-acetoxy-3,5-dimethylaniline hydrochloride (258 mg) and triethylamine (0.17 ml), followed by refluxing for 20 minutes. The mixture was washed with water, then dried (MgSO4), followed by distilling off the solvent. To the residue was added ether to afford the above-titled compound as colorless crystals (280 mg).

Workup

  1. additionwas added dropwise to triethylamime (0.14 ml)
  2. temperaturerefluxed for 30 minutes
  3. temperatureby refluxing for 20 minutes
  4. washThe mixture was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationby distilling off the solvent
  7. additionTo the residue was added ether

Sources & evidence

ORD record
ord-e395a4606132456aa4f369f795be6d0e
Source dataset
uspto-grants-1994_04
Patent number
US05300646

Reaction notes

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