2-Aminothiazole → HCID 15005409, compound

HRID 892775Notes

Reaction equation

HRID 892775 reaction equation
Br[CH:2]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[C:3](=O)[CH3:4].[NH2:14][C:15]1[S:16][CH:17]=[CH:18][N:19]=1.C(N(CC)CC)C>C(O)CCC>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([C:2]2[N:19]3[C:15]([S:16][CH:17]=[CH:18]3)=[N:14][C:3]=2[CH3:4])=[CH:7][CH:8]=1)#[N:11]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 15005405HCID 15005405, compound

Product 1

HCID 15005409HCID 15005409, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A solution of 4-(1-bromo-2-oxopropyl)benzonitrile (1 g, 4 mmol) in n-butanol (3 ml) was added in a single portion to a hot (110° C.), stirred solution of 2-aminothiazole in n-butanol (3 ml). After refluxing for 2 hours, triethylamine (0.5 ml, 4 mmol) was added and heating was resumed for a further 2 hours. All volatiles were evaporated and the residue was chromatographed on silica gel, eluting with ethyl acetate:hexane:diethylamine (5:14:1) to afford an off-white solid (0.34 g, 35%), m.p. 88°-91° C.

Workup

  1. temperatureAfter refluxing for 2 hours
  2. temperatureheating
  3. customAll volatiles were evaporated
  4. customthe residue was chromatographed on silica gel
  5. washeluting with ethyl acetate:hexane:diethylamine (5:14:1)

Sources & evidence

ORD record
ord-b18eb0bb2326401e9418140f87de1ada
Source dataset
uspto-grants-1992_06
Patent number
US05120747

Reaction notes

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