Dichloromethane → HCID 53785563, compound

HRID 582044Notes

Reaction equation

HRID 582044 reaction equation
[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)[CH2:2][CH3:3].O.[OH:14][N:15]1[C:19]2C=CC=CC=2N=N1.Cl[CH2:25]Cl.C(N(CC)CC)C>O>[CH3:25][O:14][N:15]([CH3:19])[C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 1376014-Propylbenzoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 53785563HCID 53785563, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-n-propylbenzoic acid (10.0 g), 1-hydroxybenzotriazole hydrate (8.20 g), 1-(3-N,N-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (21.5 g) and dichloromethane (1000 ml) was treated dropwise with triethylamine (42.6 ml) and N,-dimethylhydroxylamine hydrochloride (6.6 g). The mixture was stirred overnight at room temperature and then treated with water (700 ml). The organic layer was separated, washed with 2N aqueous hydrochloric acid (4×500 ml) and then saturated aqueous sodium bicarbonate solution (4×500 ml). The organic phase was dried (MgSO4) and concentrated to give the title compound as a clear oil (10.8 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with 2N aqueous hydrochloric acid (4×500 ml)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-72335c073e684e3dbd37896ce5da91bf
Source dataset
uspto-grants-1999_07
Patent number
US05922747

Reaction notes

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