1,1,1-Trimethoxy-2-chloroethane → 1006601-77-9

HRID 1987996Notes

Reaction equation

HRID 1987996 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:13][CH2:14][C:15](OC)(OC)OC>C(O)C>[Cl:13][CH2:14][C:15]1[O:12][C:11]2[C:2](=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=[CH:9][CH:10]=2)[N:1]=1

Participants

4

Reactant 2

HCID 1447021,1,1-Trimethoxy-2-chloroethaneHCID 205248Anthranilic acid, 3-hydroxy-, methyl ester

Product 1

HCID 689963151006601-77-9Yield 66.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 2-amino-3-hydroxybenzoate (3.5 g, 20.70 mmol) and 2-chloro-1,1,1-trimethoxyethane (3.0 mL, 22.06 mmol) in ethanol (30 mL) was stirred under reflux for 6 h. The reaction mixture was cooled to ambient temperature and the solvent volume was reduced under reduced pressure approximately to ⅔ of initial volume. The precipitate formed was filtered, washed with ether (3×10 mL), and dried under vacuum to afford methyl 2-(chloromethyl)benzoxazole-4-carboxylate (3.1 g, 66%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.05 (dd, J=8.0, 1.0 Hz, 1H), 7.78 (dd, J=9.0, 1.0 Hz 1H), 7.47 (t, J=5.0 Hz, 1H), 4.84 (s, 2H), 4.04 (s, 3H); (APCI+) m/z 226 (M+H).

Workup

  1. temperatureunder reflux for 6 h
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with ether (3×10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-8f135f0d77f840be9920d437092da142
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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