O-Phenylenediamine → HCID 49805202, compound

HRID 1020429Notes

Reaction equation

HRID 1020429 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].F[P-](F)(F)(F)(F)F.S1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=C1.C(N(CC)CC)C.[Br:43][C:44]1[C:45]([CH3:63])=[C:46]([CH:60]=[CH:61][CH:62]=1)[C:47]([NH:49][CH2:50][C:51]1[CH:59]=[CH:58][C:54]([C:55]([O-])=[O:56])=[CH:53][CH:52]=1)=[O:48]>CN(C=O)C>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][C:55](=[O:56])[C:54]1[CH:58]=[CH:59][C:51]([CH2:50][NH:49][C:47](=[O:48])[C:46]2[CH:60]=[CH:61][CH:62]=[C:44]([Br:43])[C:45]=2[CH3:63])=[CH:52][CH:53]=1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 86663231HCID 86663231, compound2×HCID 178486080HCID 178486080, compound

Product 1

HCID 49805202HCID 49805202, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenylenediamine (217 mg, 2.01 mmol), 1H-benzothiazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (BOP; 667 mg, 1.51 mmol) and triethyl amine (203 mg, 2.01 mmol) were dissolved in 3 mL of DMF. 350 mg of the 4-((3-bromo-2-methylbenzamido)methyl)benzoate obtained in step 2 (1.01 mmol) was added thereto and stirred at room temperature overnight. The resulting mixture was subjected to thin layer chromatography to monitor the amount of 4-((3-bromo-2-methylbenzamido)methyl)benzoate consumed, and DMF was removed under a reduced pressure. 50 mL of saturated sodium bicarbonate was added to the resulting mixture, extracted with methylene chloride (3×75 mL) and the separated organic layer was dried over anhydrous magnesium sulfate. The residue was dissolved in methylene chloride and n-pentane was added thereto. The resulting solid thus obtained was filtered and washed with ethanol to obtain the title compound (231 mg, 52%).

Workup

  1. customconsumed
  2. customDMF was removed under a reduced pressure
  3. addition50 mL of saturated sodium bicarbonate was added to the resulting mixture
  4. extractionextracted with methylene chloride (3×75 mL)
  5. dry with materialthe separated organic layer was dried over anhydrous magnesium sulfate
  6. dissolutionThe residue was dissolved in methylene chloride
  7. additionn-pentane was added
  8. customThe resulting solid thus obtained
  9. filtrationwas filtered
  10. washwashed with ethanol

Sources & evidence

ORD record
ord-1ac68cab456b499fbfcfa0ce2efbf996
Source dataset
uspto-grants-2014_05
Patent number
US08716326B2

Reaction notes

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