Water → HCID 12369474, compound

HRID 1729631Notes

Reaction equation

HRID 1729631 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH:11]([C:13]2[N:14]=[C:15]([C:21](=[S:23])[NH2:22])[NH:16][C:17]=2[N+:18]([O-:20])=[O:19])[CH3:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:25][CH2:26][C:27]([CH2:29]Cl)=O.O.O1CCOC[CH2:33]1>>[CH3:33][N:16]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:13][N:14]=[C:15]1[C:21]1[S:23][CH:29]=[C:27]([CH2:26][Cl:25])[N:22]=1.[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([S:7]([O:10][CH:11]([C:13]2[N:14]=[C:15]([C:21]3[S:23][CH:29]=[C:27]([CH2:26][Cl:25])[N:22]=3)[NH:16][C:17]=2[N+:18]([O-:20])=[O:19])[CH3:12])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 107931,3-DichloroacetoneHCID 312751,4-DioxaneHCID 136354634HCID 136354634, compound

Product 2

HCID 12369474HCID 12369474, compoundHCID 136354633HCID 136354633, compound

Conditions

Temperature
130 °C

Procedure

The 2-thiocarbamyl compounds from Example 1 (0.27 mole) and 1,3-dichloroacetone (0.55 mole) in dioxan (55 ml.) were stirred and heated at 130° C. for 2 hours. The mixture was poured into water, the resultant precipitate washed with hot water and dried to yield 2-(1-methyl-5-nitroimidazol-2-yl)-4-chloromethylthiazole m.p. 160°-2° C. and 2-(1-p-toluenesulphonyloxyethyl-5-nitroimidazol-2-yl)-4-chloromethylthiazole respectively. The 1-p-toluenesulphonyloxy compound, on treatment as described at the end of Example 2, yielded 2-(1-vinyl-5-nitroimidazol-2-yl)-4-chloromethylthiazole.

Workup

  1. washthe resultant precipitate washed with hot water
  2. customdried

Sources & evidence

ORD record
ord-12af5ba4d6f3469f8e4025006c77b437
Source dataset
uspto-grants-1976_11
Patent number
US03989690

Reaction notes

Loading…