Acetic Acid → HCID 85857180, compound

HRID 2250815Notes

Reaction equation

HRID 2250815 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]Br)[C:11]=3[N:12]=2)=[CH:4][CH:3]=1.C1N2CN3CN(C2)CN1C3.C(O)(=[O:31])C>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([CH:17]=[O:31])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 69102910HCID 69102910, compound

Product 1

HCID 85857180HCID 85857180, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-4-(bromomethy)benzoxazole (P0002; 2.0 g) and hexamethylenetetramine (1.27 g) in acetic acid (15 ml) and water (7.5 ml) was refluxed for 3 hours and evaporated. EtOAc and an aqueous NaHCO3 solution were added, and the organic layer was separated, dried, and evaporated. The residue (1.47 g) was purified by silica gel (25 g) column chromatography eluting with hexane-CH2Cl2-EtOAc (5:1:1) to give pale yellow crystals of 2-(4-chlorophenyl)benzoxazole-4-carbaldehyde (P0003; 0.89 g).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customevaporated
  3. additionEtOAc and an aqueous NaHCO3 solution were added
  4. customthe organic layer was separated
  5. customdried
  6. customevaporated
  7. customThe residue (1.47 g) was purified by silica gel (25 g) column chromatography
  8. washeluting with hexane-CH2Cl2-EtOAc (5:1:1)

Sources & evidence

ORD record
ord-4fcf30da009f44a587bb6bd9e6d3c5a7
Source dataset
uspto-grants-2008_01
Patent number
US07317107B2

Reaction notes

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