Diethylamine → 3-Chloro-N,N-diethyl-2-hydroxybenzamide

HRID 1159069Notes

Reaction equation

HRID 1159069 reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH2:12]([N:14]([CH2:15][CH3:16])[C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[C:3]=1[OH:11])[CH3:13]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 745853-Chlorosalicylic acidHCID 2724699PyBOP

Product 1

HCID 685919563-Chloro-N,N-diethyl-2-hydroxybenzamideYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 3-chloro-2-hydroxybenzoic acid (7.2 g, 42 mmol) and diethyl amine (15.2 g, 209 mmol) in dry CH2Cl2 (200 mL) was added benzotriazol-1-yloxy tripyrrolidinophosphonium hexafluorophosphate (22.8 g, 44 mmol) in dry CH2Cl2 (200 mL). The reaction was stirred overnight and then quenched with 6M HCl. The layers were separated and the aqueous layer was extracted with EtOAc (3×100 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a brown oil. The oil was purified by flash chromatography (silica gel, 0-50% EtOAc in hexanes) to yield 7.6 g of the desired product as a reddish oil.

Workup

  1. customquenched with 6M HCl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (3×100 mL)
  4. dry with materialdried over Na2SO4
  5. customThe oil was purified by flash chromatography (silica gel, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ae8501aa055a41ec9f1c68fc95a1f7a9
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

Loading…