Triethylamine → HCID 178419362, compound

HRID 1401247Notes

Reaction equation

HRID 1401247 reaction equation
Cl.[Br:2][C:3]1[CH:13]=[CH:12][C:6]([C:7](=[NH:11])OCC)=[CH:5][CH:4]=1.[CH:14]([NH:16][NH2:17])=O.C(N(CC)CC)C>>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]2[NH:11][CH:14]=[N:16][N:17]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 12229HydrazinecarboxaldehydeHCID 19017302Ethyl 4-bromobenzimidate hydrochloride

Product 1

HCID 178419362HCID 178419362, compoundYield 48.3%

Conditions

Temperature
85 °C

Procedure

Ethyl 4-bromobenzimidate hydrochloride (35.6 g, 135 mmol), formic hydrazide (16.16 g, 269 mmol) and triethylamine (75 mL, 538 mmol) were combined in a screw capped flask and heated to 85° C. for 16 h. The solution was condensed under reduced pressure to afford a solid, which was partitioned between water and ethyl acetate (3×), dried over magnesium sulfate and solvent removed under reduced pressure. The resulting solid was sonicated with 20% ethyl acetate in hexanes, filtered and dried to afford the title compound (14.6 g, 65.2 mmol, 48% yield). MS (ESI) m/z 224.1 [M]+, 226.1 [M+2]+.

Workup

  1. customcapped flask
  2. customcondensed under reduced pressure
  3. customto afford a solid, which
  4. customwas partitioned between water and ethyl acetate (3×)
  5. dry with materialdried over magnesium sulfate and solvent
  6. customremoved under reduced pressure
  7. customThe resulting solid was sonicated with 20% ethyl acetate in hexanes
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-a4dc0992baba4b5aa14cfd7a0216fe56
Source dataset
uspto-grants-2014_12
Patent number
US08907087B2

Reaction notes

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