Dichloromethane → HCID 53785563, compound

HRID 1416422Notes

Reaction equation

HRID 1416422 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.ON1C2C=CC=CC=2N=N1.ClCCl.Cl.[CH3:28][NH:29][O:30][CH3:31]>O.C(N(CC)CC)C>[CH3:31][O:30][N:29]([CH3:28])[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

7

Reactant 4

HCID 6344DichloromethaneHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 1376014-Propylbenzoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 53785563HCID 53785563, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

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,O-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 (4×500ml). The organic phase was dried (MgSO4) and concentrated to give the title compound as a clear oil (10.8 g). 1H-NMR (CDCl3): δ=0.95(t,3H), 1.65(m,2H), 2.60(t,2H), 3.36(s,3H), 3.58(s,3H), 7.20(d,2H), 7.60(d, 2H) ppm.

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-eef7c574b4bc48d89f0b8b2d895478e5
Source dataset
uspto-grants-1999_06
Patent number
US05912357

Reaction notes

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