Sodium Methoxide → (3-Bromo-5-iodophenyl)-thiourea

HRID 1010629Notes

Reaction equation

HRID 1010629 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Br:20])[CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[Br:20][C:15]1[CH:14]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[CH:18]=[C:17]([I:19])[CH:16]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 578136521-Benzoyl-3-(3-bromo-5-iodophenyl)-thiourea

Product 1

HCID 57813682(3-Bromo-5-iodophenyl)-thioureaYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred suspension of 1-Benzoyl-3-(3-bromo-5-iodophenyl)-thiourea (20.70 g, 0.0449 mol) in methanol (303 ml) was treated with sodium methoxide (2.42 g, 0.0449 mol) and stirred at ambient temperature for 4 h. The resultant suspension was evaporated to dryness at reduced pressure. The residue was mixed with water (500 ml) and extracted with ethyl acetate (3×200 ml) which was dried (MgSO4) and the solvent removed in vacuo to give a residue which was triturated with 40-60° petroleum ether/diethyl ether (1:1) to afford (3-Bromo-5-iodophenyl)-thiourea as an off-white solid (14.35 g, 89%).

Workup

  1. customThe resultant suspension was evaporated to dryness at reduced pressure
  2. additionThe residue was mixed with water (500 ml)
  3. extractionextracted with ethyl acetate (3×200 ml) which
  4. dry with materialwas dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a residue which
  7. customwas triturated with 40-60° petroleum ether/diethyl ether (1:1)

Sources & evidence

ORD record
ord-ec356922f60f4dc7b0572fa8765eaeee
Source dataset
uspto-grants-2011_07
Patent number
US07977340B2

Reaction notes

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