Bromoacetic Acid → HCID 117823870, compound

HRID 59126Notes

Reaction equation

HRID 59126 reaction equation
[CH:1]1([CH2:4][O:5][CH2:6][C:7]2[NH:12][C:11](=S)[NH:10][C:9](=[O:14])[CH:8]=2)[CH2:3][CH2:2]1.BrCC(O)=[O:18].[OH-].[Na+]>CCO.O>[CH:1]1([CH2:4][O:5][CH2:6][C:7]2[NH:12][C:11](=[O:18])[NH:10][C:9](=[O:14])[CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6227Bromoacetic AcidHCID 14798Sodium HydroxideHCID 117824033HCID 117824033, compound

Product 1

HCID 117823870HCID 117823870, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

6-[(Cyclopropylmethoxy)methyl]-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one (10.3 g, 48.5 mmol) was added to bromoacetic acid (21.5 g, 155 mmol, 3.2 eq) in EtOH (108 mL) and H2O (441 mL). The reaction mixture was refluxed for 16 h then cooled down to rt and basified to pH˜10 with sodium hydroxide (3 M, aq). The mixture was concentrated in vacuo and hydrochloric acid (aq, 10%) was added. The mixture was cooled to 0° C. The precipitate was isolated by filtration and dried to give the title compound as a solid (3.5 g, 37%).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. concentrationThe mixture was concentrated in vacuo and hydrochloric acid (aq, 10%)
  3. additionwas added
  4. customThe precipitate was isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-46c754c58ea941b6a092d2ed98a61f48
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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