Triethylamine → HCID 135678132, compound

HRID 2413791Notes

Reaction equation

HRID 2413791 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]2=[N:10]1.C(N(CC)CC)C.[C:26](Cl)(=[O:30])[C:27]([CH3:29])=[CH2:28]>C(Cl)Cl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:26](=[O:30])[C:27]([CH3:29])=[CH2:28])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]2=[N:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 135710958HCID 135710958, compound

Product 1

HCID 135678132HCID 135678132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 10.4 g. (0.04 mole) of 2-(2-hydroxy-5-aminophenyl)-5-chlorobenzotriazole and 4.1 g. triethylamine in 400 ml. methylene chloride (no preservative) was added at 0°-5° C., under nitrogen, with stirring, 4.2 g. methacryloyl chloride in 30 ml. methylene chloride. The dropwise addition required about 30 minutes. The mixture was stirred at 0°-5° C. for an additional 30 minutes and then at room temperature for one hour. The mixture was then washed with equal volumes of water, 5% hydrochloric acid and water. The organic phase was dried over magnesium sulfate and poured onto a 2" column of silica gel (120 g.) which had been slurry packed with methylene chloride. The column was eluted with methylene chloride and 100 ml. fractions were taken. The fractions were examined by thin layer chromatography (TLC) on silica gel plates using 1:5, ethyl acetate:chloroform as the developing solvent. The fractions containing the product (r.f. 0.36) were combined and evaporated. The residual solid was crystallized from ethanol to give 2.2 g. of product, m.p. 204°-205° C.

Workup

  1. additionThe dropwise addition required about 30 minutes
  2. stirringThe mixture was stirred at 0°-5° C. for an additional 30 minutes
  3. washThe mixture was then washed with equal volumes of water, 5% hydrochloric acid and water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. additionpoured onto a 2" column of silica gel (120 g.) which
  6. washThe column was eluted with methylene chloride and 100 ml
  7. additionThe fractions containing the product (r.f. 0.36)
  8. customevaporated
  9. customThe residual solid was crystallized from ethanol
  10. customto give 2.2 g

Sources & evidence

ORD record
ord-2b6a3905438840708129014bd1d15d63
Source dataset
uspto-grants-1988_01
Patent number
US04719248

Reaction notes

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