Water → 4-(Chloromethyl)-1,3-thiazole

HRID 258867Notes

Reaction equation

HRID 258867 reaction equation
C1(C)C=CC(S(OC([C:13]2[N:14]=[C:15]([C:21](=[S:23])[NH2:22])[NH:16][C:17]=2[N+:18]([O-:20])=[O:19])C)(=O)=O)=CC=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.[Cl:25][CH2:26][C:15]1[N:14]=[CH:13][S:23][CH:21]=1

Participants

6

Reactant 4

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

Product 2

HCID 27632904-(Chloromethyl)-1,3-thiazoleHCID 12369474HCID 12369474, 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-441c113a41b748f4b95f9d1ba58b47bf
Source dataset
uspto-grants-1977_07
Patent number
US04035390

Reaction notes

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