Methanol → HCID 70381427, compound

HRID 1607109Notes

Reaction equation

HRID 1607109 reaction equation
Cl.C[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[C:14]2[C:18]([OH:20])=[O:19])=[CH:6][CH:5]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH2:3].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[C:14]2[C:18]([OH:20])=[O:19])=[CH:6][CH:5]=1.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[C:14]2[C:18]([OH:20])=[O:19])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 13478003HCID 13478003, compound

Product 1

HCID 70381427HCID 70381427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 1.1 g (0.0037 mole) of 1-[3-(4-methoxyphenyl)propyl]imidazole-2-carboxylic acid hydrochloride in 100 ml of CH2Cl2 at 5° was treated with a solution of 2.8 g (0.011 mole) of BBr3 in 7 ml of CH2Cl2. The mixture was allowed to warm to 22°, and stirred for 5 hr. Methanol was cautiously added, and when a virgorous reaction was over, all solvents were evaporated. A residue was dissolved in 10 ml of H2O and the pH was adjusted to 3.5 with aqueous NaHCO3. The product crystallized, was filtered, washed with H2O and dried. Recrystallization from methanol gave 1-[3-(4-hydroxyphenyl)propyl]imidazole-2-carboxylic acid, hemihydrate, 0.65 g (71%), mp 136° (dec).

Workup

  1. temperatureto warm to 22°
  2. customwhen a virgorous reaction
  3. customwere evaporated
  4. dissolutionA residue was dissolved in 10 ml of H2O
  5. customThe product crystallized
  6. filtrationwas filtered
  7. washwashed with H2O
  8. customdried
  9. customRecrystallization from methanol

Sources & evidence

ORD record
ord-4348971dd95d4f049ce0db6aac912172
Source dataset
uspto-grants-1989_09
Patent number
US04863944

Reaction notes

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