Triethylamine → HCID 59441650, compound

HRID 1014230Notes

Reaction equation

HRID 1014230 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[C:8](N)[CH:7]=[CH:6][C:5]=1[N+:11]([O-])=O.C([N:18](CC)CC)C.CN(C1C=CC=CN=1)C.Cl.[CH3:33][N:34]([CH2:36][C:37](Cl)=[O:38])[CH3:35].C(=O)(O)[O-].[Na+]>ClCCl>[NH2:11][C:5]1[CH:6]=[C:7]([NH:18][C:37](=[O:38])[CH2:36][N:34]([CH3:35])[CH3:33])[CH:8]=[CH:9][C:4]=1[O:3][C:2]([F:15])([F:14])[F:1]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 516892Sodium BicarbonateHCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 53418146HCID 53418146, compound

Product 1

HCID 59441650HCID 59441650, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-trifluoromethoxy-4-amino nitro benzene (5.00 g, 22.5 mmol) in dichloromethane (200 mL) was added triethylamine (12.2 mL, 90 mmol, 4.0 equiv.), dimethylaminopyridine (ca 500 mg) and dimethylaminoacetyl chloride hydrochloride (5.3 g, 33.8 mmol, 1.50 equiv.). The resulting clear solution was stirred 24 hours and was poured into saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, taken to a residue under reduced pressure, and purified by chromatography on SiO2 (0 to 10% methonal/CH2CL2) to give N1-[3-amino-4-(trifluoromethoxy)phenyl]-N2,N2-dimethylglycinamide (4.54 g, 14.8 mmol, 66% yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.26 (s, 6 H), 3.11 (s, 2 H), 7.67 (dd, J=8.97, 1.28 Hz, 1 H), 8.08 (dd, J=9.06, 2.65 Hz, 1 H), 8.60 (d, J=2.74 Hz, 1 H), 10.40 (s, 1 H).

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. custompurified by chromatography on SiO2 (0 to 10% methonal/CH2CL2)

Sources & evidence

ORD record
ord-19904990a528447f81dab9082c45fcd1
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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