Hydrochloric Acid → 6-[m-(Furfurylamino)phenyl]-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

HRID 597576Notes

Reaction equation

HRID 597576 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:15][N:14]3[C:10]([S:11][CH2:12][CH2:13]3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[CH:16](=O)[C:17]1[O:21][CH:20]=[CH:19][CH:18]=1.C([BH3-])#N.[Na+].Cl>CO.C(O)(=O)C>[CH2:16]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:15][N:14]3[C:10]([S:11][CH2:12][CH2:13]3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1)[C:17]1[O:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7362FurfuralHCID 30386693-AminolevamisoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 214456356-[m-(Furfurylamino)phenyl]-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 4.4 g. (0.020 mole) of 6-(m-aminophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole, 2.1 g. (0.022 mole) furfural, 3.5 ml. acetic acid and 50 ml. methanol are placed in a reaction flask along with some molecular sieves. To this 0.63 g. (0.01 mole) of sodium cyanoborohydride is added slowly and the mixture stirred two hours. The mixture is now acidified to pH 1 with hydrochloric acid. A solid material is removed by trituration and the solvent evaporated leaving an oily residue.

Workup

  1. additionA mixture of 4.4 g
  2. customA solid material is removed by trituration
  3. customthe solvent evaporated
  4. customleaving an oily residue

Sources & evidence

ORD record
ord-3b6b42b30cdb4a41a28da061da19bd31
Source dataset
uspto-grants-1977_03
Patent number
US04014892

Reaction notes

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