Triethylamine → HCID 178495792, compound

HRID 78445Notes

Reaction equation

HRID 78445 reaction equation
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([C:13]([OH:15])=O)=[CH:5][CH:4]=[C:3]3[CH2:2]1.C1C2=C3C(=CC=C2)C(C(Cl)=O)=CC=C3C1.[CH3:31][O:32][CH2:33][CH2:34][N:35]1[C:39]([CH3:40])=[C:38]([CH3:41])[S:37][C:36]1=[NH:42].CCN(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=[N:42]\[C:13]([C:6]1[C:7]2[C:12]3[C:3]([CH2:2][CH2:1][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:5]=1)=[O:15]

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 178495792HCID 178495792, 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-ffdaa7244df34f0fb035b8160557da21
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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