3,5-Bis(trifluoromethyl)benzoyl chloride → HCID 87849648, compound

HRID 1351392Notes

Reaction equation

HRID 1351392 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@@H:16]([OH:17])[CH2:15][CH2:14][C@@H:13]3[C@H:9]2[CH2:10][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12]3)=[CH:4][CH:3]=1.[F:25][C:26]([F:41])([F:40])[C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[C:30](Cl)=[O:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:25][C:26]([F:40])([F:41])[C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([C:36]([F:39])([F:37])[F:38])[CH:35]=1)[C:30]([O:17][C@H:16]1[CH2:15][CH2:14][C@@H:13]2[C@@H:9]([CH2:10][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12]2)[C@@H:8]1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:31]

Participants

5

Reactant 2

HCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 69474024HCID 69474024, compound

Product 1

HCID 87849648HCID 87849648, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.75 g (14.0 mmol) of the intermediate of step B in dry methylene chloride under nitrogen atmosphere at RT was added 4.71 g (17.0 mmol) of 3,5-bis(trifluoromethyl)-benzoyl chloride, 2.4 mL (17.3 mmol) TEA and a catalytic amount of DMAP. The resulting mixture was stirred at RT for 2 hr then transferred to a separatory funnel, washed with saturated. aq. NaHCO3 and brine. The combined organic layers dried over magnesium sulfate, filtered and the solvent evaporated under vacuum to afford the crude title compound which was used without further purification. 1H-NMR (CDCl3): δ: 8.63 (1H, s), 8.19 (2H, s), 7.25 (2H, m), 7.00 (2H, m), 5.22 (1H, m), 3.59–3.33 (2H, m), 3.30–3.20 (2H, m), 2.83 (1H, t,J=12.7 Hz), 2.62 (1H, m), 2.43 (1H, m), 2.20 (1H, m), 2.02 (1H, m), 1.90–1.70 (2H, m), 1.55, 1.47 (9H, two singlets).

Workup

  1. customthen transferred to a separatory funnel
  2. washwashed with saturated
  3. dry with materialThe combined organic layers dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-1c3caf279f7b472794903765f7a2ed02
Source dataset
uspto-grants-2007_05
Patent number
US07217731B2

Reaction notes

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