2-(Benzyloxy)-5-bromobenzaldehyde → HCID 22105521, compound

HRID 1455942Notes

Reaction equation

HRID 1455942 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C:19]1[S:20][C:21]([C:24]([NH:26][CH2:27][CH2:28][CH3:29])=[O:25])=[N:22][N:23]=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH2:11][NH:18][C:19]1[S:20][C:21]([C:24]([NH:26][CH2:27][CH2:28][CH3:29])=[O:25])=[N:22][N:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7330872-(Benzyloxy)-5-bromobenzaldehydeHCID 22105591HCID 22105591, compound

Product 1

HCID 22105521HCID 22105521, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-benzyloxy-5-bromobenzaldehyde (4.2 g) and 2-amino-N-propyl-1,3,4-thiadiazole-5-carboxamide (2.7 g) in toluene (200 mL) was heated under reflux for 2 hours. The solvent was evaporated and residue was dissolved in ethanol (100 mL) and was heated under reflux for 3 hours then allowed to cool to ambient temperature. Sodium borohydride (0.53 g) was added and the reaction mixture was stirred for 16 hours then poured into water (500 mL). The aqueous mixture was extracted 4 times with ethyl acetate (50 mL each time), the combined extracts were washed 3 times with water (100 mL each time) and dried (MgSO4). The residue obtained on removal of the solvent was subjected to chromatography on silica, eluting with a mixture of ethyl acetate and dichloromethane (1/5 v/v), to give 2-[N-(2-benzyloxy-5-bromobenzyl)amino]-N-propyl-1,3,4-thiadiazole-5-carboxamide, yield 0.81 g, mp 154° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was evaporated
  4. dissolutionresidue was dissolved in ethanol (100 mL)
  5. temperaturewas heated
  6. temperatureunder reflux for 3 hours
  7. additionSodium borohydride (0.53 g) was added
  8. additionthen poured into water (500 mL)
  9. extractionThe aqueous mixture was extracted 4 times with ethyl acetate (50 mL each time)
  10. washthe combined extracts were washed 3 times with water (100 mL each time)
  11. dry with materialdried (MgSO4)
  12. customThe residue obtained on removal of the solvent
  13. washeluting with a mixture of ethyl acetate and dichloromethane (1/5 v/v)

Sources & evidence

ORD record
ord-8285785b9f50450caa0f4888254b04c4
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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