Ammonia → 4-(3-Pyridinyl)-2-thiazolamine

HRID 653609Notes

Reaction equation

HRID 653609 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br.Br[CH2:7][C:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=O.N>O>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:8]2[N:1]=[C:2]([NH2:4])[S:3][CH:7]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 2723790ThioureaHCID 27762343-(2-Bromoacetyl)pyridine hydrobromide

Product 1

HCID 1548934-(3-Pyridinyl)-2-thiazolamineYield 97.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of thiourea (70,4 g) in water (265 ml) was added dropwise to a stirred solution of 3-bromoacetylpyridine hydrobromide (251,6 g) in water (1 1) over 15 minutes. The solution, which turned yellow and became quite hot, was allowed to stand for one hour, and was then basified by addition of aqueous ammonia. The resulting solid was filtered off, washed with water, and dried in vacuo at 65° C. to give 4-(pyridin-3-yl)-thiazol-2-amine, (155 g) Mp 200° C.

Workup

  1. filtrationThe resulting solid was filtered off
  2. washwashed with water
  3. customdried in vacuo at 65° C.

Sources & evidence

ORD record
ord-5978978f974d465fb2dfd0623526bdf9
Source dataset
uspto-grants-1992_07
Patent number
US05128340

Reaction notes

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