Triethylamine → HCID 178495801, compound

HRID 1037867Notes

Reaction equation

HRID 1037867 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]([CH3:10])=[C:8]([CH3:11])[S:7][C:6]1=[NH:12].CCN(CC)CC.[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>C1COCC1>[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](/[N:12]=[C:6]1\[S:7][C:8]([CH3:11])=[C:9]([CH3:10])[N:5]\1[CH2:4][CH2:3][O:2][CH3:1])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 668517233-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Product 1

HCID 178495801HCID 178495801, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 126A (0.20 g, 1.1 mmol), Et3N (0.45 mL, 3.2 mmol) and 2-chlorobenzoyl chloride (Aldrich, 0.26 g, 1.4 mmol) in 15 mL THF were processed as in Example 132 to afford the title compound (0.13 g, 0.40 mmol, 37% yield). 1H NMR (300 MHz, CD3OD) δ ppm 2.28 (s, 3H), 2.32 (s, 3H), 3.31 (s, 3H), 3.76 (t, J=5.3 Hz, 2H), 4.42 (t, J=5.1 Hz, 2H), 7.30-7.46 (m, 3H), 7.77-7.83 (m, 1H); MS (DCI/NH3) m/z 325 (M+H)+; Anal. calculated for C15H17ClN2O2S: C, 55.46; H, 5.28; N, 8.62. Found: C, 55.59; H, 4.81; N, 8.47.

Sources & evidence

ORD record
ord-fb83467d8c2942f7bd40699f8243465a
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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