Hydrogen Bromide → 2-[4,5-Bis-(p-methoxyphenyl)-thiazol-2-ylthio]-acetaldehyde

HRID 544662Notes

Reaction equation

HRID 544662 reaction equation
C([O:3][C:4](=O)[CH:5]([S:8][C:9]1[S:10][C:11]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:13]=1)C=O)C.Br>C(O)(=O)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[N:13]=[C:9]([S:8][CH2:5][CH:4]=[O:3])[S:10][C:11]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 543019562-[4,5-Bis-(p-methoxyphenyl)-thiazol-2-ylthio]-2-formylacetic acid ethyl ester

Product 1

HCID 132096722-[4,5-Bis-(p-methoxyphenyl)-thiazol-2-ylthio]-acetaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.0 g of 2-[4,5-bis-(p-methoxyphenyl)-thiazol-2-ylthio]-2-formylacetic acid ethyl ester are dissolved in 50 ml of acetic acid, 10 ml of 43% strength hydrobromic acid are added and the mixture is heated at 80° for 4 hours. The mixture is concentrated to dryness by evaporation under reduced pressure, and the residue is dissolved in 200 ml of ethyl acetate, washed twice with 50 ml of saturated sodium bicarbonate solution each time and with water, dried over magnesium sulphate and concentrated to dryness by evaporation. The crude product is recrystallised from hexane/diethyl ether (55 ml+10 ml). 2-[4,5-bis-(p-methoxyphenyl)-thiazol-2-ylthio]-acetaldehyde having a melting point of 75°-76° is obtained.

Workup

  1. temperaturethe mixture is heated at 80° for 4 hours
  2. concentrationThe mixture is concentrated to dryness by evaporation under reduced pressure
  3. dissolutionthe residue is dissolved in 200 ml of ethyl acetate
  4. washwashed twice with 50 ml of saturated sodium bicarbonate solution each time
  5. dry with materialwith water, dried over magnesium sulphate
  6. concentrationconcentrated to dryness by evaporation
  7. customThe crude product is recrystallised from hexane/diethyl ether (55 ml+10 ml)

Sources & evidence

ORD record
ord-7cae3f533ddd46688009f0690d0c1218
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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