Isopropanol → Benzoic acid, 2-chloro-5-(((1-methylethoxy)carbonyl)amino)-, 1-methylethyl ester

HRID 1938864Notes

Reaction equation

HRID 1938864 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([N:14]=[C:15]=[O:16])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[CH:17]([OH:20])([CH3:19])[CH3:18]>O1CCCC1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([O:20][CH:17]([CH3:19])[CH3:18])=[O:16])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 21470251HCID 21470251, compound

Product 1

HCID 466508Benzoic acid, 2-chloro-5-(((1-methylethoxy)carbonyl)amino)-, 1-methylethyl ester

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

NMR (CDCl3): 1.39 (6H,d), 5.26 (1H,m), 6.98-7.52 (3H,m). 1-Methylethyl 2-chloro-5-isocyanatobenzoate (3 g, 0.013 mole) in tetrahydrofuran (5 ml) was added to isopropyl alcohol (5 ml) in tetrahydrofuran (5 ml). A few drops of triethylamine were added and the reaction mixture left at ambient temperature overnight. Removal of the solvent and crystallization from isopropyl alcohol gave the title compound, m.p. 108°-109° C. (2.7 g).

Workup

  1. customRemoval of the solvent and crystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-7a7a2040e6b04ed8923fa708431a2bb2
Source dataset
uspto-grants-1997_12
Patent number
US05693827

Reaction notes

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