Water → HCID 67506130, compound

HRID 1469643Notes

Reaction equation

HRID 1469643 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.Cl[CH2:17][C:18]([NH2:20])=[O:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:12]([O:14][CH2:17][C:18](=[O:19])[NH2:20])[CH:13]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 67506130HCID 67506130, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-hydroxyisophthalic acid dimethyl ester (500 mg, 2.38 mmol) and chloroacetamide (245 mg, 2.62 mmol) in DMF (7 mL) is added potassium carbonate (986 mg, 7.14 mmol) and the mixture is stirred at room temperature for 2 days. Water is added to the mixture and then it is extracted with ethyl acetate. The organic phase is washed with water and brine and is dried over sodium sulfate. The organic solution is concentrated to one fourth volume to give a precipitate. The solid is filtered, washed with ethyl acetate and dried under reduced pressure to give 5-carbamoylmethoxyisophthalic acid dimethyl ester. MS 268.2 (M+1);); 1H-NMR (400 MHz, CDCl3); δ ppm 3.96 (s, 6H), 4.59 (s, 2H), 5.87 (s, broad, 1H), 6.55 (s, broad, 1H), 7.79 (s, 2H), 8.37 (s, 1H).

Workup

  1. extractionit is extracted with ethyl acetate
  2. washThe organic phase is washed with water and brine
  3. dry with materialis dried over sodium sulfate
  4. concentrationThe organic solution is concentrated to one fourth volume
  5. customto give a precipitate
  6. filtrationThe solid is filtered
  7. washwashed with ethyl acetate
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-191f70398636466dbc09446f7289d784
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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