2-Bromopropiophenone → HCID 20558016, compound

HRID 1660159Notes

Reaction equation

HRID 1660159 reaction equation
[CH2:1]([NH:7][C:8]([NH2:10])=[S:9])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[Br:11][CH:12]([CH3:21])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O>C(O)C>[BrH:11].[CH2:1]([NH:7][C:8]1[S:9][C:12]([CH3:21])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=1)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 164522-BromopropiophenoneHCID 7176991-(2-Furfuryl)-2-thiourea

Product 1

HCID 20558016HCID 20558016, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-furfurylthiourea (0.82 grams, 0.005 moles) and α-bromopropiophenone (1.07 grams, 0.005 moles, Aldrich Chem. Co.) in 11 ml absolute ethanol were heated to reflux temperature under nitrogen for 3 hours. After cooling to room temperature, the solvent was removed under vacuum to give a thick brown oil, which was triturated with five 35 ml portions of refluxing ethyl acetate. The ethyl acetate was reduced in volume to about 25 ml and cooled to room temperature. The precipitated solids were filtered, washed with ethyl acetate and vacuum dried over phosphorous pentoxide, yielding 0.585 grams (33%) of 2-furfurylamino-5-methyl-4-phenyl-thiazole hydrobromide, m.p. 150°-153° C.

Workup

  1. temperatureto reflux temperature under nitrogen for 3 hours
  2. customthe solvent was removed under vacuum
  3. customto give a thick brown oil, which
  4. customwas triturated with five 35 ml portions of refluxing ethyl acetate
  5. temperaturecooled to room temperature
  6. filtrationThe precipitated solids were filtered
  7. washwashed with ethyl acetate and vacuum
  8. dry with materialdried over phosphorous pentoxide

Sources & evidence

ORD record
ord-2fb5f3923dbe497787edbd608a630467
Source dataset
uspto-grants-1981_12
Patent number
US04307106

Reaction notes

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