Oxalyl chloride → HCID 23445655, compound

HRID 1067356Notes

Reaction equation

HRID 1067356 reaction equation
[CH:1]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:17](Cl)(=O)[C:18](Cl)=O.[CH2:23]([C:30]1(C)[CH:34](C)[CH:33]=[CH:32][S:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[CH2:23]([C:30]1[S:31][C:17]([CH3:18])=[C:33]([CH3:32])[C:34]=1[C:9]([C:8]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:7]=1)=[O:11])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 158950343-Cyclopentyl-p-anisic acidHCID 234456402-Benzyl-2,3-dimethylthiophene

Product 1

HCID 23445655HCID 23445655, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

The title compound was prepared according to the procedure in Example 5, step 2 using 3-cyclopentyl-p-anisic acid (5.0 g, 22.7 mmol, RN-59216-82-9), oxalyl chloride (2.4 mL, 27.2 mmol), N,N-dimethylformamide (2 drops) tin(IV) chloride (2.9 mL, 25.0 mmol) and 2-benzyl-2,3-dimethylthiophene (5.1 g, 25.0 mmol). Purification on silica gel eluting 5% EtOAc/pet. ether gave 4.8 g (52%) of the title compound as an amber oil. (DMSO-d6) δ7.61-7.54 (m, 2H), 7.24-7.14 (m, 3H), 7.08-7.02 (m, 3H), 3.87 (s, 3H), 3.84 (s, 2H), 3.42-3.30 (m, 1H), 2.26 (s, 3H), 2.00-1.85 (m, 2H), 1.81 (s, 3H), 1.74-1.58 (m, 4H), 1.48-1.36 (m, 2H). mass spectrum (EI) m/z 404 (M+). Anal. Calc. for C26H28O2S: C, 77.19, H, 6.98, N, 0.00. Found: C, 76.26, H, 7.24, N, 0.04.

Workup

  1. customThe title compound was prepared
  2. customPurification on silica gel eluting 5% EtOAc/pet. ether

Sources & evidence

ORD record
ord-f34a2371111c49d596b79fce051132c2
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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