2-Chloro-4-fluorobenzoyl chloride → HCID 69351039, compound

HRID 970738Notes

Reaction equation

HRID 970738 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:12][N:13]([CH3:27])[CH:14]1[CH2:19][CH2:18][C:17]([C:20]2[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=2)=[CH:16][CH2:15]1>>[ClH:1].[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:17]2[CH2:18][CH2:19][CH:14]([N:13]([CH3:27])[CH3:12])[CH2:15][CH:16]=2)[CH:21]=1)=[O:5]

Participants

3

Reactant 2

HCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 58852355HCID 58852355, compound

Product 1

HCID 69351039HCID 69351039, compoundYield 138.4%

Procedure

Using a method similar to example 1, using 2-chloro-4-fluorobenzoyl chloride (128 mg, 0.66 mmol) and 3-(4-dimethylamino-cyclohex-1-enyl)-phenylamine (preparation 2, 119 mg, 0.55 mmol) provides the title compound (free base 187 mg, 91%). Free base: MS (ES): m/z=373.2 (M+H)+; 1H NMR (CDCl3): δ 8.08 (s, br, 1H), 7.77 (m, 1H), 7.68 (s, br, 1H), 7.52 (d, 1H), 7.32 (t, 1H), 7.19 (m, 2H), 7.09 (m, 1H), 6.11 (m, 1H), 2.51 (m, 4H), 2.36 (s, 6H), 2.14 (m, 2H), 1.57 (m, 1H). Hydrochloride salt: Anal. cal'd for C21H22ClFN2O.HCl.0.5H2O: C, 60.29; H, 5.78; N, 6.70. Found: C, 60.17; H, 5.45; N, 6.65.

Sources & evidence

ORD record
ord-4aa2c0c437624351bd0159c734f02255
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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