Sulfuric Acid → HCID 178491962, compound

HRID 981566Notes

Reaction equation

HRID 981566 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][CH2:13][CH:14](OC)OC)=[S:11])=[CH:5][CH:4]=1.OS(O)(=O)=O>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:14]=[CH:13][N:12]=[C:10]2[SH:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 8820791-(2,2-Dimethoxyethyl)-3-(4-methoxyphenyl)thiourea2×

Product 1

HCID 178491962HCID 178491962, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10 g (.06 mole) of p-methoxyphenyl isothiocyanate in 100 ml of CHCl3 was treated with 6.3 g (.06 mole) of aminoacetaldehyde dimethyl acetal. The solvent was evaporated and the residue was recrystallized from ethanol to yield N-(p-methoxyphenyl)-N'-(β,β-dimethoxyethyl)thiourea, 9.2 g (57%). A suspension of this thiourea in a solution of 5 ml of concentrated H2SO4 and 20 ml of H2O was refluxed for 3 hours. The mixture was cooled and a solid was filtered, washed with H2O and dried. Recrystallization from ethanol gave 1-(4-methoxyphenyl)-2-mercaptomidazole, 4.9 g (70%), mp 215-7° . The compound can be deprotected, for example, as illustrated in Example 5 and 6, below, to prepare the phenol, Y is --OH.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe mixture was cooled
  3. filtrationa solid was filtered
  4. washwashed with H2O
  5. customdried
  6. customRecrystallization from ethanol
  7. customgave 1-(4-methoxyphenyl)-2-mercaptomidazole, 4.9 g (70%), mp 215-7°

Sources & evidence

ORD record
ord-d800c5a4529c4b1daa295bf5c953bff1
Source dataset
uspto-grants-1991_02
Patent number
US04992459

Reaction notes

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