Water → HCID 178480144, compound

HRID 1379580Notes

Reaction equation

HRID 1379580 reaction equation
[SH:1][C:2]1[N:6]([CH3:7])[CH:5]=[CH:4][N:3]=1.C([Li])CCC.[F:13][C:14]([F:24])([F:23])[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.[OH2:25]>C1COCC1>[OH:25][C:16]1([CH:19]=[CH:20][CH:21]=[CH:22][CH:15]1[C:14]([F:24])([F:23])[F:13])[CH2:17][C:5]1[N:6]([CH3:7])[C:2]([SH:1])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 178418339ButyllithiumHCID 178480602HCID 178480602, compound

Product 1

HCID 178480144HCID 178480144, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-mercapto-3-methylimidazole in dry THF (100 ml) at 0° C. was added an n-butyl lithium solution (2.5M, 35.1 ml) over 10 minutes. The mixture was allowed to warm to room temperature and stirred for 3 hours. A white solid formed during this time. The temperature was brought down to 0° C. and 2-trifluoromethylbenzaldehyde (7.63 g) was added slowly over 15 minutes. The color turned dark brown. After 30 minutes, water (4 ml) was added to quench the reaction. The mixture was allowed to stir overnight. The 4-(1-hydroxy-2'-trifluoromethylbenzyl)-2-mercapto-3-methylimidazole formed (8.8 g) was collected by filtration, washed with 1:1 diethyl ether:hexanes and air dried.

Workup

  1. customA white solid formed during this time
  2. customwas brought down to 0° C.
  3. waitAfter 30 minutes
  4. customto quench
  5. customthe reaction
  6. stirringto stir overnight

Sources & evidence

ORD record
ord-661d40c55dff4c568283afebd972a9aa
Source dataset
uspto-grants-1997_09
Patent number
US05672567

Reaction notes

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