Sodium Carbonate → HCID 178418385, compound

HRID 1905638Notes

Reaction equation

HRID 1905638 reaction equation
C(OC1(O)C=CC(C(=O)CBr)=CC1C(N)=O)C1C=CC=CC=1.NCCC[N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[N:28]1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[N:28]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 42201883-(benzotriazol-1-yl)propan-1-amineHCID 86738829HCID 86738829, compound

Product 1

HCID 178418385HCID 178418385, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 17.5 gm of 2-benzyloxy-5-bromoacetyl salicylamide, 17.6 gm of 1-(3-aminopropyl)-1H-benzotriazole, 6 gm of sodium carbonate and 150 ml of ethyl acetate was refluxed for 1.5 hours. After separation of the inorganic constituents, the mother liquor was evaporated, the residue was dissolved in a 100 ml of acetonitrile, and the solution was acidified with 5 gm of oxalic acid. The precipitated 1-[3-(3-carbamoyl-4-benzyloxy-β-oxophenethylamino)-propyl]-1-H-benzotriazole oxalate was collected by suction of filtration converted with aqueous ammonia into the base (m.p. 186°-188° C.) and reduced in 100 ml of ethanol with sodium borohydride to form 1-(3-carbamoyl-4-benzyloxy-β-hydroxyphenethylamino)propyl]-1-H-benzotriazole.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. customAfter separation of the inorganic constituents
  3. customthe mother liquor was evaporated
  4. dissolutionthe residue was dissolved in a 100 ml of acetonitrile
  5. filtrationThe precipitated 1-[3-(3-carbamoyl-4-benzyloxy-β-oxophenethylamino)-propyl]-1-H-benzotriazole oxalate was collected by suction of filtration

Sources & evidence

ORD record
ord-3e5162706a984a5e8efbbbdf406424ac
Source dataset
uspto-grants-1987_03
Patent number
US04647563

Reaction notes

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