Dimethyl-p-toluidine → HCID 22713535, compound

HRID 351844Notes

Reaction equation

HRID 351844 reaction equation
[CH:1]1([C:4]2[N:8]=[C:7]([C:9]3[N:10]=[CH:11][N:12]4[C:18]=3[CH2:17][NH:16][C:15](=O)[C:14]3[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:13]4=3)[O:6][N:5]=2)[CH2:3][CH2:2]1.CN(C)C1C=CC(C)=CC=1.P(Br)(Br)(Br)=O.[NH2:41][NH2:42]>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[N:8]=[C:7]([C:9]3[N:10]=[CH:11][N:12]4[C:18]=3[CH2:17][N:16]=[C:15]([NH:41][NH2:42])[C:14]3[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:13]4=3)[O:6][N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7471Dimethyl-p-toluidineHCID 9321HydrazineHCID 24613Phosphorus oxybromideHCID 22713513HCID 22713513, compound

Product 1

HCID 22713535HCID 22713535, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(3-Cyclopropyl-[1,2,4]oxadiazol-5-yl)-8-methoxy-4,5-dihydro-2,5,10b-triaza-benzo[e]azulen-6-one (1 g, 3 mmol) and N,N-dimethyl-p-toluidine (0.856 mL, 5.9 mmol) were mixed in toluene (25 mL), treated with phosphoryl bromide (0.935 g, 3.3 mmol), and refluxed for 15 h. Toluene was evaporated and the residue extracted with CH2Cl2 (50 mL) and water (50 mL). The organic layer was dried, evaporated, redissolved in THF (50 mL), and treated with a 1 M solution of anhydrous hydrazine in TBF (10 mL, 10 mmol) at reflux overnight. The mixture was evaporated and directly chromatographed on silica gel in CH2Cl2/MeOH 10:1. One obtained a light brow solid (0.4 g, 38%). m/z 352 (MH+).

Workup

  1. temperaturerefluxed for 15 h
  2. customToluene was evaporated
  3. extractionthe residue extracted with CH2Cl2 (50 mL) and water (50 mL)
  4. customThe organic layer was dried
  5. customevaporated
  6. dissolutionredissolved in THF (50 mL)
  7. temperatureat reflux overnight
  8. customThe mixture was evaporated
  9. customdirectly chromatographed on silica gel in CH2Cl2/MeOH 10:1

Sources & evidence

ORD record
ord-769b73dc691547a58e4d1f262a3798f1
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Reaction notes

Loading…