Diethylamine → HCID 68675116, compound

HRID 1993066Notes

Reaction equation

HRID 1993066 reaction equation
C(Cl)(=O)C(Cl)=O.[F:7][C:8]([F:38])([F:37])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([CH:34]=[CH:35][CH:36]=2)[CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH3:33])([CH2:30][CH:31]=[CH2:32])[C:27](O)=[O:28])=[CH:22][CH:21]=2)=[CH:11][CH:10]=1.[CH2:39]([NH:41][CH2:42][CH3:43])[CH3:40].CCN(CC)CC>ClCCl>[F:37][C:8]([F:38])([F:7])[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[C:17]([CH:34]=[CH:35][CH:36]=2)[CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([CH3:33])([CH2:30][CH:31]=[CH2:32])[C:27]([N:41]([CH2:42][CH3:43])[CH2:39][CH3:40])=[O:28])=[CH:24][CH:25]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68673706HCID 68673706, compound

Product 1

HCID 68675116HCID 68675116, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Oxalyl chloride (57.7 mg, 0.45 mmol) was added dropwise to 49.5 (100 mg, 0.23 mmol) in anhydrous dichloromethane (4 mL). The resulting mixture was refluxed in a sealed tube at 50° C. overnight. The dichloromethane was removed under a stream of N2. Anhydrous ether (2 mL) was added dropwise, followed by diethyl amine (50 mg, 0.69 mmol) and Et3N (70 mg, 0.69 mmol). The mixture was refluxed overnight. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified via flash chromatography (25% ethyl acetate in hexanes). 82 mg of 49.6 was obtained. MS ESI m/e: 496 (M−H). 1H NMR (500 MHz) (CDCl3) δ 7.72 (4H, s); 7.69 (1H, s); 7.6-7.5 (3H, m); 7.14 (2H, d, J=8.5 Hz); 7.05 (2H, d, J=8.5 Hz); 5.7-5.6 (1H, m); 5.15 (2H, s); 5.03-5 (2H, m); 3.5-3.2 (2H, m); 3.0-2.9 (2H, m); 2.74-2.64 (2H, m); 1.62 (3H, s); 1.13 (3H, s); 0.72 (3H, s).

Workup

  1. customThe dichloromethane was removed under a stream of N2
  2. additionAnhydrous ether (2 mL) was added dropwise
  3. temperatureThe mixture was refluxed overnight
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe resulting residue was purified via flash chromatography (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a2a2d7e27b3e4eb081baacadf68aff92
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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