Water → Methyl 4-((5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-YL)carbamoyl)benzoate

HRID 2076427Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1.CN(C=O)C.[CH3:19][C:20]1([CH3:33])[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:26]2[CH:25]=[C:24]([NH2:32])[CH:23]=[CH:22][C:21]1=2.O>O=S(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:32][C:24]2[CH:23]=[CH:22][C:21]3[C:20]([CH3:33])([CH3:19])[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:26]=3[CH:25]=2)=[O:10])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Terephthalic acid monomethyl ester (194 mg, 1.08 mmol) was dissolved in SOCl2 (5.39 mL) at 0° C. A drop of DMF was added and the mixture was stirred for 30 min. The SOCl2 was removed under vacuum and the crude acid chloride was dissolved in pyridine (12.5 mL). 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamine 6 (200 g, 0.98 mmol) and DMAP (12 mg, 0.1 mmol) was added and the mixture was heated at 60° C. for 2 h with stirring. The mixture was poured into H2O and the product was extracted with EtOAc. Them organic layer was washed successively with HCl 2M, saturated NaHCO3, saturated NaCl, dried over MgSO4 and filtrated to give after evaporation N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-terephthalamic acid methyl ester 7 (316 mg, 88% yield) as a white solid.

Workup

customThe SOCl2 was removed under vacuum
dissolutionthe crude acid chloride was dissolved in pyridine (12.5 mL)
stirringwith stirring
extractionthe product was extracted with EtOAc
washThem organic layer was washed successively with HCl 2M, saturated NaHCO3, saturated NaCl
dry with materialdried over MgSO4
filtrationfiltrated
customto give

Sources & evidence

ORD record: ord-b4a8623f583642d8b5ca7fd31f80c53d
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923579B2

Reaction notes

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