Triethylamine → HCID 58723691, compound

HRID 1993580Notes

Reaction equation

HRID 1993580 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.Cl.[CH3:24][NH:25][CH3:26].CCN(CC)CC>CN(C=O)C.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([N:25]([CH3:26])[CH3:24])=[O:8])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 65578Oxalyl chlorideHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 58723691HCID 58723691, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In an ice bath under N2-atmosphere, 3-nitro-5-trifluoromethyl-benzoic acid (Lancaster; 11.8 g, 50 mmol), CH2Cl2 (150 ml), 3 drops of DMF and oxalylchloride ( 7.0 ml, 81 mmol) are mixed and then stirred for 2.5 h at rt. The resulting solution is concentrated in vacuo. The residue is dissolved in CH2Cl2 (170 ml) and added dropwise to an ice cooled solution of dimethylamine hydrochloride (4.5 g, 55 mmol) and NEt3 (21 ml; 0.15 mol) in CH2Cl2 (100 ml). After stirring for 15 h at rt, the mixture is worked up as described in Stage 134.3, giving the title compound as an oil: MS: [M+1]+=263; 1H-NMR (CDCl3): 8.53 (s, 1H), 8.47 (s, 1H), 8.03 (s, 1H), 3.18 (s, 3H), 3.04 (s, 3H).

Workup

  1. concentrationThe resulting solution is concentrated in vacuo
  2. dissolutionThe residue is dissolved in CH2Cl2 (170 ml)
  3. stirringAfter stirring for 15 h at rt

Sources & evidence

ORD record
ord-313926f44dad4d0a9ba70764d4ad5515
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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