Benzene → HCID 19787184, compound

HRID 1657221Notes

Reaction equation

HRID 1657221 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:21]=[C:20]([CH2:22][CH3:23])[S:19][C:10]=2[N:11]([CH3:18])[C:12](=[O:17])[C:13]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C1C=CC=CC=1.[F:47][C:48]1[CH:54]=[C:53]([F:55])[CH:52]=[CH:51][C:49]=1[NH2:50].C([N:58]([CH2:61]C)CC)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:21]=[C:20]([CH2:22][CH3:23])[S:19][C:10]=2[N:11]([CH3:18])[C:12](=[O:17])[C:13]=1[NH:58][C:61]([NH:50][C:49]1[CH:51]=[CH:52][C:53]([F:55])=[CH:54][C:48]=1[F:47])=[O:31]

Participants

6

Reactant 5

HCID 241BenzeneHCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 199401P,P-Diphenylphosphinic azideHCID 19787178HCID 19787178, compound

Product 1

HCID 19787184HCID 19787184, compoundYield 44.4%

Procedure

To a mixture of 4-(2-chlorophenyl)-6,7-dihydro-2 -ethyl-7-methyl-6-oxothieno[2,3-b]pyridine-5-carboxylic acid (347 mg), diphenylphosphoryl azide (330 mg) and benzene (4 ml) was added dropwise triethylamine (0.14 ml). The mixture was stirred at room temperature for 30 minutes, stirred under reflux for 30 minutes and then 2,4-difluoroaniline (0.12 ml) was added. The mixture was refluxed for 4 hours, washed with water, dried over MgSO4, and then the solvent was distilled off. The residue was chromatographed on a silica gel and eluted with chloroform/ethyl acetate/metanol (9:1:0.25). The solvent was distilled off to obtain N-[4-(2-chlorophenyl)-6,7-dihydro-2-ethyl-7-methyl-6-oxothieno[2,3-b]pyridin-5-yl]-N'-(2,4-difluorophenyl)urea as colorless powder (210 mg, 44.4%).

Workup

  1. stirringstirred
  2. temperatureunder reflux for 30 minutes
  3. temperatureThe mixture was refluxed for 4 hours
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. distillationthe solvent was distilled off
  7. customThe residue was chromatographed on a silica gel
  8. washeluted with chloroform/ethyl acetate/metanol (9:1:0.25)
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-9e99db981df842dda802786a0d99641c
Source dataset
uspto-grants-1993_10
Patent number
US05256782

Reaction notes

Loading…