Tetrahydrofuran → HCID 2774059, compound

HRID 615868Notes

Reaction equation

HRID 615868 reaction equation
O1CCCC1.[NH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1.[Br:18][CH:19]([CH3:23])[C:20](Br)=[O:21]>C(N(CC)CC)C>[Br:18][CH:19]([CH3:23])[C:20]([NH:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)=[O:21]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 403022-Amino-4-phenylthiazoleHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 2774059HCID 2774059, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into 50 ml of tetrahydrofuran, were added 3.5 g of 2-amino-4-phenylthiazole and 2.0 g of triethylamine. The mixture was cooled to 0°--5° C. Then, 4.3 g of α-bromopropionylbromide was dropped to the solution mixture. After the completion of the dropwise addition, the solution mixture was stirred at room temperature for 1 hour. Then, the reaction mixture was concentrated under reduced pressure. The residue was taken up in chloroform and washed with water. Upon removal of chloroform, a crude reaction product was obtained. It was thereafter subjected to silica gel chromatography and then eluted with a chloroform/methyl alcohol (40:1) mixed solvent. It was then recrystallized from an ether/cyclohexane mixed solvent, thereby obtaining 4.2 g of 2-(α-bromopropionylamino)-4-phenylthiazole.

Workup

  1. temperatureThe mixture was cooled to 0°--5° C
  2. additionAfter the completion of the dropwise addition
  3. concentrationThen, the reaction mixture was concentrated under reduced pressure
  4. washwashed with water
  5. customUpon removal of chloroform
  6. customa crude reaction product
  7. customwas obtained
  8. washeluted with a chloroform/methyl alcohol (40:1)
  9. additionmixed solvent
  10. customIt was then recrystallized from an ether/cyclohexane mixed solvent

Sources & evidence

ORD record
ord-6723f302a8e645e59382ffa343e3a998
Source dataset
uspto-grants-1985_02
Patent number
US04501750

Reaction notes

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