Bromine → HCID 15661170, compound

HRID 2051030Notes

Reaction equation

HRID 2051030 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]3[CH2:10][CH2:11][CH2:12][N:7]3[C:6]=2[CH:13]=1.[Br:14]Br.C(Cl)(Cl)Cl.CO.[K+].[Br-]>C(O)(=O)C.O.C(=O)(O)[O-].[Na+]>[Br:14][C:3]1[C:2]([CH3:1])=[CH:13][C:6]2[N:7]3[CH2:12][CH2:11][CH2:10][C:8]3=[N:9][C:5]=2[CH:4]=1

Participants

8

Reactant 4

HCID 24408BromineHCID 253877Potassium BromideHCID 15661169HCID 15661169, compoundHCID 21584188Chloroform methanol

Product 1

HCID 15661170HCID 15661170, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1 q (5.81 mmol) of 22 in 30 mL of qlacial acetic acid, heated at 100°, was added 300 μl of bromine in 3 mL glacial acetic acid. After the addition, the reaction mixture was heated at 100°-110° C. for 4 hours. The cooled reaction mixture was diluted with I00 mL of water and neutralized with aqueous sodium bicarbonate. The product crystallized from solution as a light yellow solid. Yield upon drying the collected solid Was 1.37 g (88%). Recrystallization from chloroform/hexane afforded analytically pure 23: mp 167°-170° C.; TLC (chloroform/methanol, [90:10]), Rf =0.56, IR(KBr pellet), 2949, 2929, 1581, 1521, 1482, 1461, 1448, 1418, 1291, 872 cm-1 ; 1H NMR (dimethyl sulfoxide-d6) δ71, and 7.43 (2 H, 2× s, aromatic protons), 4.04 (2 H, t, J~7 Hz, C(1) methylene), 2.91 (2 H, t, J~7 Hz), C(3) methylene), 2.59 (2 H, quintet, J~7 Hz, C(2) methylene), 2.39 (3 H, s, 7-methyl); mass spectrum (EI mode) m/z 250 and 252 (P+, 79Br and P+, 81Br), 171 (P+ -Br). Anal. Calcd for C11H11BrN2.0.25 H2O: C, 51.47; H, 4.31; N, 10.91. Found: C, 51.56; H, 4.24; N, 10.78.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated at 100°-110° C. for 4 hours
  3. customThe cooled reaction mixture
  4. customThe product crystallized from solution as a light yellow solid
  5. customYield
  6. customupon drying the collected solid
  7. customRecrystallization from chloroform/hexane
  8. customafforded analytically pure 23

Sources & evidence

ORD record
ord-ca0d36a204184dd5bd5803fce7971eb2
Source dataset
uspto-grants-1991_05
Patent number
US05015742

Reaction notes

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