Acetone → HCID 20130085, compound

HRID 845719Notes

Reaction equation

HRID 845719 reaction equation
ClCN[C:4](=[O:6])[O-].[CH:7]1[CH:8]=[CH:9][C:10]2[N:15]=[C:14]([C:16]3[N:20]=[CH:19][S:18][CH:17]=3)[NH:13][C:11]=2[CH:12]=1.[I-:21].[Na+].C[C:24](C)=[O:25]>>[I:21][CH2:4][O:6][C:24]([N:15]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:12][C:11]=2[N:13]=[C:14]1[C:16]1[N:20]=[CH:19][S:18][CH:17]=1)=[O:25]

Participants

5

Reactant 4

HCID 180AcetoneHCID 5238Sodium IodideHCID 5430ThiabendazoleHCID 21864633HCID 21864633, compound

Product 1

HCID 20130085HCID 20130085, compound

Procedure

The above chloromethylcarbamate of thiabendazole (1 g) was dissolved in acetone (50 ml) and stirred at room temperature with sodium iodide (1 g) for 72 hours. The acetone was evaporated off. The residue taken in chloroform was washed with water, aqueous sodium bisulfite and water. The chloroform solution was evaporated to furnish 1.2 g of a light yellow solid which tended to decompose on attempting crystallize from EtOAc. NMR (CDCl3) δ6.03 (2H, s, OCH2I), 7.3-8.1 (5H, m, aromatic) and 8.96 (1H, d, J=3 Hz, aromatic).

Workup

  1. customThe acetone was evaporated off
  2. washwas washed with water, aqueous sodium bisulfite and water
  3. customThe chloroform solution was evaporated

Sources & evidence

ORD record
ord-45c9e3330f034aed9fc8a4f1ab205491
Source dataset
uspto-grants-1988_07
Patent number
US04760057

Reaction notes

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