Dabco → HCID 20610368, compound

HRID 852552Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.C1N2CCN(CC2)C1.[CH3:24][N:25]([CH3:29])[C:26](Cl)=[S:27]>CN(C=O)C>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:12]([O:14][C:26](=[S:27])[N:25]([CH3:29])[CH3:24])[CH:13]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

o a solution of 5-hydroxy-isophthalic acid dimethyl ester (D42) (21 g, 100 mmol, 1 equiv) in DMF (300 ml) at room temperature was added DABCO (14.6 g, 130 mmol, 1.3 equiv) followed by dimethylthiocarbamoyl chloride (14.8 g, 120 mmol, 1.2 equiv). The resulting mixture was stirred at room temperature for 16 h and at 60° C. for 2 h, then cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt and H2O and the aqueous phase re-extracted with AcOEt. The combined organic solution was washed sequentially with 5% aqueous citric acid solution, 2N aqueous NaOH solution and brine, then dried over MgSO4 and concentrated in vacuo to give 5-dimethylthiocarbamoyloxy-isophthalic acid dimethyl ester (D55) (23.5 g, 79%) as a pale yellow oil. [M+H]+=298.0, RT=3.06 min

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
customThe residue was partitioned between AcOEt and H2O
extractionthe aqueous phase re-extracted with AcOEt
washThe combined organic solution was washed sequentially with 5% aqueous citric acid solution, 2N aqueous NaOH solution and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a5d22f5c0d2144f58d95134c2e7be8a2
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253198B2

Reaction notes

Loading…