Chloroacetic Acid → HCID 86756603, compound

HRID 323521Notes

Reaction equation

HRID 323521 reaction equation
[OH-:1].[Na+].[SH:3][C:4]1[NH:9][N:8]([SH:10])[CH:7]=[C:6]([SH:11])[N:5]=1.Cl[CH2:13][C:14]([OH:16])=[O:15].Cl.[CH2:18]([OH:20])[CH3:19]>O>[C:14]([CH2:13][S:3][C:4]1[NH:9][N:8]([S:10][CH2:19][C:18]([OH:1])=[O:20])[CH:7]=[C:6]([S:11][CH2:13][C:14]([OH:16])=[O:15])[N:5]=1)([OH:16])=[O:15]

Participants

7

Reactant 5

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 178527746HCID 178527746, compound

Product 1

HCID 86756603HCID 86756603, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Aqueous solution of sodium hydroxide 17.66 g (0.44 mol) in 30 ml of water was added drop by drop to the mixture of 2,4,6-trimercapto-1,3,4-triazine 23.0 g (0.13 mol), chloroacetic acid 54.0 g (0.44 mol) and ethanol 300 ml with stirring at room temperature. After 20 minutes it was heated to 50° C., and aqueous solution of sodium hydroxide 17.6 g (0.44 mol) in 30 ml of water was added drop by drop slowly. It was cooled off to room temperature after 3 hours stirring at 50° C., and then water was added till reaction liquid became uniform, and hydrochloric acid was added for neutralization. Resulted crystal was filtrated and recrystallized in methanol to obtain 2,4,6 tris-carboxymethylthio-1,3,4-triazine in amount of 35.4 g (0.10 mol). Yield 76%.

Workup

  1. temperatureAfter 20 minutes it was heated to 50° C.
  2. temperatureIt was cooled off to room temperature after 3 hours
  3. stirringstirring at 50° C.
  4. customResulted crystal
  5. filtrationwas filtrated
  6. customrecrystallized in methanol

Sources & evidence

ORD record
ord-9b0469e4183b4c3ba5e7178ac496cdb5
Source dataset
uspto-grants-2001_04
Patent number
US06214533B1

Reaction notes

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