Triethylamine → HCID 86618911, compound

HRID 1037866Notes

Reaction equation

HRID 1037866 reaction equation
C1C2=C3C(=CC=C2)C(C(O)=O)=CC=C3C1.[CH2:16]1[C:26]2=[C:27]3[C:22](=[CH:23][CH:24]=[CH:25]2)[C:21]([C:28](Cl)=[O:29])=[CH:20][CH:19]=[C:18]3[CH2:17]1.[CH3:31][O:32][CH2:33][CH2:34][N:35]1[C:39]([CH3:40])=[C:38]([CH3:41])[S:37][C:36]1=N.CC[N:45](CC)CC>S(Cl)(Cl)=O.C1COCC1>[CH3:31][O:32][CH2:33][CH2:34][N:35]1[C:39]([CH3:40])=[C:38]([CH3:41])[S:37]/[C:36]/1=[C:19]1\[CH:18]2[C:27]3[C:22]([C:21]([C:28]([NH2:45])=[O:29])=[CH:20]\1)=[CH:23][CH:24]=[CH:25][C:26]=3[CH2:16][CH2:17]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 976195-Acenaphthoic acidHCID 45923436Acenaphthene-5-carbonyl chloride2×HCID 668517233-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Product 1

HCID 86618911HCID 86618911, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

The acenaphthene-5-carboxylic acid (Aldrich, 0.29 g, 1.4 mmol) in 5 mL of thionyl chloride was converted to acenaphthene-5-carbonyl chloride using the method described in Example 134A. The product of Example 126A (0.20 g, 1.1 mmol), Et3N (0.3 mL, 2.2 mmol) and acenaphthene-5-carbonyl chloride in 30 mL THF were processed as in Example 134B to afford the title compound (87 mg, 0.24 mmol, 22% yield). 1H NMR (300 MHz, CD3OD) δ ppm 2.28 (d, J=0.7 Hz, 3H), 2.33 (d, J=0.7 Hz, 3H), 3.33 (s, 3H), 3.42 (s, 4H), 3.84 (t, J=5.3 Hz, 2H), 4.51 (t, J=5.3 Hz, 2H), 7.30-7.36 (m, 2H), 7.52 (dd, J=8.6, 7.0 Hz, 1H), 8.43 (d, J=7.5 Hz, 1H), 8.81 (d, J=8.8 Hz, 1H); MS (DCI/NH3) m/z 367 (M+H)+; Anal. calculated for C21H22N2O2S: C, 68.82; H, 6.05; N, 7.64. Found: C, 68.63; H, 5.72; N, 7.40.

Sources & evidence

ORD record
ord-b3b14764b5ba4e1d8f7ce207d223f99a
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

Loading…