Propanal → N2-Mesityl-N7,N7-dipropyl-1,3-benzoxazole-2,7-diamine

HRID 2235529Notes

Reaction equation

HRID 2235529 reaction equation
[C:1]1([CH3:22])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[O:11][C:12]2[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1.[CH3:23]O.[CH:25](=O)[CH2:26][CH3:27].[BH3-]C#N.[Na+].C(O[CH2:37][CH3:38])(=O)C>C(O)(=O)C>[C:1]1([CH3:22])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[O:11][C:12]2[C:18]([N:19]([CH2:23][CH2:37][CH3:38])[CH2:25][CH2:26][CH3:27])=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

7

Reactant 5

HCID 527PropanalHCID 887MethanolHCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydrideHCID 68581419N-Mesityl-7-nitro-1,3-benzoxazol-2-amine

Product 1

HCID 58896475N2-Mesityl-N7,N7-dipropyl-1,3-benzoxazole-2,7-diamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a flask was added 0.10 g (0.34 mmol) of N-mesityl-7-nitro-1,3-benzoxazol-2-amine and 40 ml of methanol. The flask was purged with nitrogen followed by the addition of 0.01 g of 10% palladium on carbon. The flask was evacuated and pressurized to 2-3 psig hydrogen and stirred for 1 h. After completion as determined by HPLC, the reaction was filtered through GF/F filter paper. The filtrate was transferred to round bottom flask and 0.1 ml (1.7 mmol) of propionaldehyde, 0.1 g (1.7 mmol) of NaBH3CN and 1 ml of acetic acid were added. The mixture was stirred overnight, then diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via Biotage chromatography eluting with 5% methanol/dichloromethane gave 0.11 g (90% for 2 steps) of product.

Workup

  1. customThe flask was purged with nitrogen
  2. additionfollowed by the addition of 0.01 g of 10% palladium on carbon
  3. customThe flask was evacuated
  4. filtrationthe reaction was filtered through GF/F
  5. filtrationfilter paper
  6. customThe filtrate was transferred to round bottom flask
  7. stirringThe mixture was stirred overnight
  8. washwashed with water
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. filtrationFiltration, removal of solvent and purification of the residue via Biotage chromatography
  11. washeluting with 5% methanol/dichloromethane
  12. customgave 0.11 g (90% for 2 steps) of product

Sources & evidence

ORD record
ord-3c1f45537b2f4cacad0bf73b85e3ecf9
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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