2,5-Dichlorobenzoic acid → HCID 178495805, compound

HRID 1037873Notes

Reaction equation

HRID 1037873 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.ClC1C=CC(Cl)=CC=1C(Cl)=O.S(Cl)(Cl)=O.[CH3:27][O:28][CH2:29][CH2:30][N:31]1[C:35]([CH3:36])=[C:34]([CH3:37])[S:33][C:32]1=[NH:38].CCN(CC)CC>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](/[N:38]=[C:32]1\[S:33][C:34]([CH3:37])=[C:35]([CH3:36])[N:31]\1[CH2:30][CH2:29][O:28][CH3:27])=[O:6]

Participants

7

Reactant 5

HCID 57842,5-Dichlorobenzoic acidHCID 8471TriethylamineHCID 179452,5-Dichlorobenzoyl chloride2×HCID 24386Thionyl ChlorideHCID 668517233-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Product 1

HCID 178495805HCID 178495805, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 2,5-dichlorobenzoic acid (Aldrich, 0.28 g, 1.4 mmol) was converted to 2,5-dichlorobenzoyl chloride with 5 mL of thionyl chloride using the method described in Example 134A. The product of Example 126A (0.20 g, 1.1 mmol), Et3N (0.45 mL, 3.2 mmol) and 2,5-dichlorobenzoyl chloride in 15 mL THF were processed using the method described in Example 132 to afford the title compound (0.10 g, 0.28 mmol, 26% yield). 1H NMR (300 MHz, CDCl3) δ ppm 2.25 (d, J=1.0 Hz, 3H), 2.28 (d, J=1.0 Hz, 3H), 3.31 (s, 3H), 3.76 (t, J=5.3 Hz, 2H) 4.36 (t, J=5.3 Hz, 2H), 7.28 (d, J=2.4 Hz, 1H), 7.32-7.36 (m, 1H), 7.94 (d, J=2.4 Hz, 1H); MS (DCI/NH3) m/z 359 (M+H)+; Anal. calculated for C15H16Cl2N2O2S: C, 50.15; H, 4.49; N, 7.80. Found: C, 50.22; H, 4.15; N, 7.63.

Sources & evidence

ORD record
ord-ab4ba02f7d804e0d998abfec46c91fdd
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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