Diethyl Ether → HCID 12926140, compound

HRID 615158Notes

Reaction equation

HRID 615158 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][CH2:12]OCC.Cl.[CH2:17]([OH:19])[CH3:18].[CH2:20]([C:22]([CH3:24])=[O:23])[CH3:21]>O1CCCC1>[OH:19][C:17]1[CH:24]=[C:22]([OH:23])[CH:20]=[CH:21][C:18]=1[C:11]1[N:1]=[C:2]2[N:6]([CH:12]=1)[C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[S:3]2

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 6569Methyl Ethyl KetoneHCID 8706Benzo(d)thiazol-2-amineHCID 21887872Ethanol hydrochloride

Product 1

HCID 12926140HCID 12926140, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.8 g of 2-aminobenzothiazole and 7.2 g of 2,4-diacetoxy-α-bromoacetophenone in 100 ml of methyl ethyl ketone was refluxed for 3 hours. After cooling the reaction mixture, 50 ml of ether was added to the reaction mixture, the precipitates formed were filtered away, and the mother liquor was concentrated under reduced pressure. The residue formed was dissolved in 10 ml of tetrahydrofuran and 10 ml of ether and then the solution was acidified by the addition of a hydrogen chloride-ethanol solution. Crystals formed which were recovered by filtration, dried and then refluxed together with 50 ml of methylcellosolve for 5 hours. The reaction mixture was alkalified by the addition of concentrated aqueous ammonia and then cooled to form crystals, which were recovered by filtration and recrystallized from tetrahydrofuran-n-hexane to provide 1 g of 2-(2,4-dihydroxyphenyl)imidazo[2,1-b]benzothiazole.

Workup

  1. additionwas added to the reaction mixture
  2. customthe precipitates formed
  3. filtrationwere filtered away
  4. concentrationthe mother liquor was concentrated under reduced pressure
  5. customThe residue formed
  6. customCrystals formed which
  7. filtrationwere recovered by filtration
  8. customdried
  9. temperaturerefluxed together with 50 ml of methylcellosolve for 5 hours
  10. additionThe reaction mixture was alkalified by the addition of concentrated aqueous ammonia
  11. temperaturecooled
  12. customto form crystals, which
  13. filtrationwere recovered by filtration
  14. customrecrystallized from tetrahydrofuran-n-hexane

Sources & evidence

ORD record
ord-05cbd0bd883f4464b30127fef1149093
Source dataset
uspto-grants-1985_02
Patent number
US04497817

Reaction notes

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