Triethylamine → HCID 178495793, compound

HRID 78443

Reaction equation

HRID 78443 reaction equation
[O:1]1[C:5]2[C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.O1C2C(C(Cl)=O)=CC=CC=2CC1.S(Cl)(Cl)=O.[CH3:29][O:30][CH2:31][CH2:32][N:33]1[C:37]([CH3:38])=[C:36]([CH3:39])[S:35][C:34]1=[NH:40].CCN(CC)CC>C1COCC1.CCOC(C)=O>[CH3:29][O:30][CH2:31][CH2:32][N:33]1[C:37]([CH3:38])=[C:36]([CH3:39])[S:35]/[C:34]/1=[N:40]\[C:10]([C:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)=[O:12]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27950142,3-Dihydro-1-benzofuran-7-carboxylic acidHCID 27950162,3-Dihydro-1-benzofuran-7-carbonyl chloride2×HCID 668517233-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Product 1

HCID 178495793HCID 178495793, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 2,3-dihydrobenzofuran-7-carboxylic acid (TCI-US, 0.25 g, 1.4 mmol) was converted to 2,3-dihydrobenzofuran-7-carbonyl 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 (0.3 mL, 2.2 mmol) and the freshly prepared 2,3-dihydrobenzofuran-7-carbonyl chloride in 30 mL THF were processed as in Example 134B. Purification of the crude material via recrystallization with 50% hexanes:EtOAc gave the title compound (0.12 g, 0.36 mmol, 34% yield). 1H NMR (300 MHz, CD3OD) δ ppm 2.25 (s, 3H), 2.30 (s, 3H), 3.22 (t, J=8.8 Hz, 2H), 3.31 (s, 3H), 3.81 (t, J=5.3 Hz, 2H), 4.44 (t, J=5.3 Hz, 2H), 4.64 (t, J=8.8 Hz, 2H), 6.86 (t, J=7.5 Hz, 1H), 7.32 (dd, J=7.3, 1.2 Hz, 1H), 7.93 (dd, J=8.0, 0.8 Hz, 1H); MS (DCI/NH3) m/z 333 (M+H)+; Anal. calculated for C17H20N2O3S.0.1H2O: C, 61.09; H, 6.09; N, 8.38. Found: C, 60.99; H, 5.91; N, 8.25.

Workup

  1. customPurification of the crude material
  2. customvia recrystallization with 50% hexanes

Sources & evidence

ORD record
ord-c92914153a104907ae9077d9926d5e07
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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