4,5-Dihydro-2-thiazolamine → HCID 2813255, compound

HRID 1381683Notes

Reaction equation

HRID 1381683 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([CH3:13])=[O:12])=[CH:6][CH:5]=1)=O.BrBr.[NH2:16][C:17]1[S:18][CH2:19][CH2:20][N:21]=1>C(Cl)Cl.O>[C:11]([NH:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]2[N:16]=[C:17]3[N:21]([CH:1]=2)[CH2:20][CH2:19][S:18]3)=[CH:5][CH:6]=1)(=[O:12])[CH3:13]

Participants

6

Reactant 3

HCID 156894,5-Dihydro-2-thiazolamineHCID 24408BromineHCID 75937N-(p-acetylphenyl)acetamide

Product 1

HCID 2813255HCID 2813255, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Acetamidoacetophenone (44 g, 0.25 mole) was suspended in 500 ml methylene chloride and treated with bromine (44 g, 0.275 mole). The reaction mixture was stirred overnight, then evaporated in vacuo. The residue was suspended in 200 ml of absolute EtOH and treated with 2-amino-4,5-dihydrothiazole (60 g, 0.59 mole). The reaction was stirred for 2 days, then taken up in water and extracted with methylene chloride. The organic phase was washed with water and then brine, and then dried over sodium sulfate. Flash column chromatography (silica, eluting with methylene chloride/methanol, 98/2) gave 6-(4-acetamidophenyl)-2,3-dihydroimidazo[2,1-b]thiazole.

Workup

  1. customevaporated in vacuo
  2. stirringThe reaction was stirred for 2 days
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with water
  5. dry with materialbrine, and then dried over sodium sulfate
  6. washFlash column chromatography (silica, eluting with methylene chloride/methanol, 98/2)

Sources & evidence

ORD record
ord-469eac780ff340deb8f83ece67de13c6
Source dataset
uspto-grants-1989_02
Patent number
US04803279

Reaction notes

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