2-Amino-4,5-diphenylthiazole → 2-Chloromethanesulfonylamino-4,5-diphenylthiazole

HRID 2399539Notes

Reaction equation

HRID 2399539 reaction equation
[Cl:1][CH2:2][S:3](Cl)(=[O:5])=[O:4].[NH2:7][C:8]1[S:9][C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1>N1C=CC=CC=1>[Cl:1][CH2:2][S:3]([NH:7][C:8]1[S:9][C:10]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 732222-Amino-4,5-diphenylthiazoleHCID 77054(Chloromethyl)sulfonyl chloride

Product 1

HCID 152327802-Chloromethanesulfonylamino-4,5-diphenylthiazoleYield 44.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.70 g of chloromethanesulfonyl chloride was dropped into a solution of 2.27 g of 2-amino-4,5-diphenylthiazole in pyridine under stirring at room temperature, and the resulting mixture was stirred as such for 2 hours. Then the reaction mixture was poured into ice-water and the crystals thus precipitated were recovered by filtration and separated with a silica gel column by using isopropyl ether and ethyl acetate as a developer. The crystals thus obtained were recrystallized from isopropyl ether/ethyl acetate to give 1.45 g of 2-chloromethanesulfonylamino-4,5-diphenylthiazole. The melting point of this product was from 201° to 203° C.

Workup

  1. stirringthe resulting mixture was stirred as such for 2 hours
  2. customthe crystals thus precipitated
  3. filtrationwere recovered by filtration
  4. customseparated with a silica gel column
  5. customThe crystals thus obtained
  6. customwere recrystallized from isopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-4c5a1d9a044c4c72a157bfe675090f8e
Source dataset
uspto-grants-1995_09
Patent number
US05449783

Reaction notes

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