Methanol → HCID 178516012, compound

HRID 981575Notes

Reaction equation

HRID 981575 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[SH:17])=[CH:5][CH:4]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[SH:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 178490136HCID 178490136, compound

Product 1

HCID 178516012HCID 178516012, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.75 g (0.007 mole) of 1-[3-(4methoxyphenyl)propyl]-2-mercaptoimidazole in 60 ml of CH2Cl2 was deprotected by treatment with a solution of 7.0 g (0.028 mole) of BBr3 in 10 ml of CH2Cl2. After 1 5 hr, the reaction mixture was cooled to 0° , and methanol was cautiously added. After a vigorous reaction subsided, the solvents were evaporated. The residue was recrystallized from ethanol to give 1-[3-(4-hydroxyphenyl)-propyl]-2-mercaptoimidazole, 1.02 g (67%), mp 185° .

Workup

  1. temperatureAfter 1 5 hr, the reaction mixture was cooled to 0°
  2. customAfter a vigorous reaction
  3. customthe solvents were evaporated
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-56a58671925b49a08816a7e8a0733bcc
Source dataset
uspto-grants-1991_02
Patent number
US04992459

Reaction notes

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