Triethylamine → HCID 59317401, compound

HRID 1691516Notes

Reaction equation

HRID 1691516 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N:10]2[N:14]=[C:13]3[CH:15]=[CH:16][C:17]([C:19]([F:22])([F:21])[F:20])=[CH:18][C:12]3=[N:11]2)[C:4]=1[OH:23].C(N(CC)CC)C.[C:31](Cl)(=[O:35])[C:32]([CH3:34])=[CH2:33]>C1COCC1>[C:31]([O:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N:10]2[N:14]=[C:13]3[CH:15]=[CH:16][C:17]([C:19]([F:22])([F:21])[F:20])=[CH:18][C:12]3=[N:11]2)[C:4]=1[OH:23])(=[O:35])[C:32]([CH3:34])=[CH2:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 66908075HCID 66908075, compound

Product 1

HCID 59317401HCID 59317401, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

In a 100 ml round bottom 3-neck flask equipped with a magnetic stirrer and nitrogen inlet was dissolved 3.58 g (11.1 mmol) 2-(hydroxymethyl)-4-methyl-6-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)phenol in 60 ml anhydrous THF. Triethylamine (5.6 ml, 40 mmol) was added and the mixture was cooled to −10° C. Methacryloyl chloride (1.373 g, 13.1 mmol) was added dropwise and the mixture was stirred for 1 hour at −10° C. followed by 20 hours at ambient temperature. The solid was filtered off and rinsed with diethyl ether and the resultant filtrate was poured into 100 ml diethyl ether and washed with 0.5 N HCl and water. The organic layer was dried with magnesium sulfate, filtered, and recrystallized with diethyl ether to give 1.90 g (44%) of a white solid. 1H NMR (CDCl3) delta: 11.17 (s, 1H, Ar—OH), 8.29 (s, 1H, Ar—H benzotriazole 4-position), 8.21 (s, 1H, Ar—H phenol 6-position), 8.06 (d, 1H, Ar—H benzotriazole 6-position), 7.69 (d, 1H, Ar—H benzotriazole 7-position), 7.29 (s, 1H, Ar—H phenol 4-position), 6.20 (s, 1H, C═C—H trans), 5.61 (s, 1H, C═C—H cis), 5.39 (s, 2H, Ar—CH2), 2.42 (s, 3H, Ar—CH3), 2.00 (s, 3H, C═C—CH3).

Workup

  1. customIn a 100 ml round bottom 3-neck flask equipped with a magnetic stirrer and nitrogen inlet
  2. waitfollowed by 20 hours at ambient temperature
  3. filtrationThe solid was filtered off
  4. washrinsed with diethyl ether
  5. additionthe resultant filtrate was poured into 100 ml diethyl ether
  6. washwashed with 0.5 N HCl and water
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. customrecrystallized with diethyl ether

Sources & evidence

ORD record
ord-a108db7c4f81428da28fe5f313f4719c
Source dataset
uspto-grants-2012_04
Patent number
US08153703B2

Reaction notes

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