5-((Bis(benzyl)amino)acetyl)salicylamide → HCID 21488956, compound

HRID 1974317Notes

Reaction equation

HRID 1974317 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:9][C:10]([C:12]1[CH:20]=[C:16]([C:17]([NH2:19])=[O:18])[C:15]([OH:21])=[CH:14][CH:13]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].Cl[CH2:31][CH2:32][CH2:33][CH2:34][O:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][O:37]1>CC(=O)CC>[CH2:22]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:31][CH2:32][CH2:33][CH2:34][O:35][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)=[C:16]([CH:20]=1)[C:17]([NH2:19])=[O:18])=[O:11])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1217275-((Bis(benzyl)amino)acetyl)salicylamideHCID 1704882H-Pyran, 2-(4-chlorobutoxy)tetrahydro-HCID 5360545Sodium

Product 1

HCID 21488956HCID 21488956, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5-(N,N-dibenzylglycyl)salicylamide, sodium salt (3.96 g), 2-(4-chlorobutoxy)tetrahydropyran (1.92 g) sodium iodide (1.40 g) and butanone (100 ml) was heated under reflux for 30 hours and filtered. The filtrate was evaporated to give an oil which crystallised from isopropanol to afford the ether as colourless crystals (2.95 g), m.p. 118°-123°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customto give an oil which
  6. customcrystallised from isopropanol
  7. customto afford the ether as colourless crystals (2.95 g), m.p. 118°-123°

Sources & evidence

ORD record
ord-d8644fe7c0a14aa78563ec3b8957f6ad
Source dataset
uspto-grants-1976_12
Patent number
US04000193

Reaction notes

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