Water → HCID 178494723, compound

HRID 1786172Notes

Reaction equation

HRID 1786172 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]2[NH:10][N:11]=[C:12]([CH2:14][O:15][CH3:16])[N:13]=2)[CH:3]=1.[Cl:17][CH2:18][C:19](Cl)=[O:20].O>C(O)(=O)C>[Cl:17][CH2:18][C:19]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[C:9]1[NH:10][N:11]=[C:12]([CH2:14][O:15][CH3:16])[N:13]=1)=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 178494724HCID 178494724, compound

Product 1

HCID 178494723HCID 178494723, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-2-(5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-phenylamine (60.6 g, 239 mmol) was dissolved in acetic acid (1.2 L) and chloroacetic chloride (40.4 mL, 508 mmol) was added dropwise at 14-16° C. over a period of 30 min. The resulting reaction mixture was stirred for 22 h at ambient temperature. After addition of water (600 mL) and stirring for another 90 min, the solid was filtered off and washed with water (600 mL). Drying in vacuo afforded the title compound (66.2 g, 83%) which was obtained as a yellow solid. MS: m/e=314.9 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringstirring for another 90 min
  3. filtrationthe solid was filtered off
  4. washwashed with water (600 mL)
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-0ca5778a5a764a9084eaaad0dc9355fc
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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