Hexamethylenetetramine → HCID 10800370, compound

HRID 1865615Notes

Reaction equation

HRID 1865615 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].N12CN3CN(CN(C3)C1)C2.FC(F)(F)[C:24](O)=[O:25]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:24]=[O:25])[C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 69725-Bromosalicylic acid

Product 1

HCID 10800370HCID 10800370, compoundYield 50%

Conditions

Temperature
100 °C

Procedure

36 g (0.17 mol) of 5-bromo-2-hydroxy-benzoic acid was dissolved in 500 mL of trifluoroacetic acid. 112 g (0.80 mol) of 1,3,5,7-tetraaza-tricyclo[3.3.1.13,7]decane (urotropine) was added and the resulting mixture heated to 100° C. for 23 h. The reaction mixture was concentrated to half its volume and the residual liquid poured into 1.8 L of dilute aqueous hydrochloric acid and stirred for 8 h at ambient temperature. The resulting precipitate was filtered off and crystallized from aqueous ethanol to afford 20.3 g (82.9 mmol, 50%) of 5-bromo-3-formyl-2-hydroxy-benzoic acid a pale yellow crystalline solid. 1H-NMR (500 MHz, d6-DMSO): δ 10.29 (s, 1H), 8.13 (d, 1H), 7.95 (d, 1H); MS: m/z 242.9+244.9 (M−H+).

Workup

  1. concentrationThe reaction mixture was concentrated to half its volume
  2. additionthe residual liquid poured into 1.8 L of dilute aqueous hydrochloric acid
  3. filtrationThe resulting precipitate was filtered off
  4. customcrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-08e9aad86768401ba29e33717ea2a999
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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