O-Xylene → HCID 135740049, compound

HRID 1699518Notes

Reaction equation

HRID 1699518 reaction equation
C[Al](C)C.[CH2:5]([NH:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH3:8].C([O:16][C:17]([C:19]([CH3:67])([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:33]=[C:32]([C:34]3[CH:39]=[CH:38][C:37]([O:40][C:41]([CH3:48])([C:43]([O:45]CC)=O)[CH3:42])=[CH:36][C:35]=3[OH:49])[N:31]=[C:30]([C:50]3[CH:55]=[CH:54][C:53]([O:56][C:57]([CH3:64])([C:59]([O:61]CC)=O)[CH3:58])=[CH:52][C:51]=3[OH:65])[N:29]=2)=[C:24]([OH:66])[CH:23]=1)[CH3:20])=O)C.C1(C)C(C)=[CH:70][CH:71]=[CH:72][CH:73]=1>CCCCCC.ClCCl>[CH2:5]([N:9]([CH2:10][CH2:11][CH2:12][CH3:13])[C:43]([C:41]([CH3:48])([O:40][C:37]1[CH:38]=[CH:39][C:34]([C:32]2[N:31]=[C:30]([C:50]3[CH:55]=[CH:54][C:53]([O:56][C:57]([CH3:64])([C:59]([N:29]([CH2:28][CH2:25][CH2:24][CH3:23])[CH2:30][CH2:50][CH2:51][CH3:52])=[O:61])[CH3:58])=[CH:52][C:51]=3[OH:65])[N:29]=[C:28]([C:25]3[CH:26]=[CH:27][C:22]([O:21][C:19]([CH3:67])([C:17]([N:31]([CH2:73][CH2:72][CH2:71][CH3:70])[CH2:32][CH2:34][CH2:35][CH3:36])=[O:16])[CH3:20])=[CH:23][C:24]=3[OH:66])[N:33]=2)=[C:35]([OH:49])[CH:36]=1)[CH3:42])=[O:45])[CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 8148DibutylamineHCID 16682925TrimethylaluminumHCID 135740159HCID 135740159, compound2×

Product 1

HCID 135740049HCID 135740049, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
130 °C

Procedure

21 ml of a 2.0 M solution of trimethylaluminium in hexane are added under argon to 5.5 g (0.042 mol) of dibutylamine in 35 ml of anhydrous dichloromethane. After 15 minutes, 10.5 g (0.014 mol) of 2,4,6-tris(4-[1-ethoxycarbonyl-1-methylethoxy]-2-hydroxyphenyl)-1,3,5-triazine (Compound 1) are added to the reaction mixture. After 1 day 10 ml of anhydrous xylene are added and the dichloromethane is distilled off. The reaction mixture is subsequently heated at 130° C. for 2 days and then 10 ml of 20% HCl are added. The reaction mixture is extracted with ethyl acetate and the organic phase is dried over magnesium sulfate. The title product is obtained after column chromatography (Compound 15: 1H NMR(CDCl3): 0.80 (t, J=7.1 Hz,9H), 0.90 (t, J=7.1 Hz,9H), 1.12-1.4 (m, 24H), 1.71 (s, 27H), 3.29-3.35 (m, 6H), 3.50-3.55 (m, 6H), 6.39-6.60 (m, 6H), 8.00-8.02 (m, 3H), 13.24 (s, 3H)) and also

Workup

  1. distillationthe dichloromethane is distilled off
  2. addition10 ml of 20% HCl are added
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. dry with materialthe organic phase is dried over magnesium sulfate

Sources & evidence

ORD record
ord-d48690578c844ed8a48f6edb60df1c00
Source dataset
uspto-grants-2002_02
Patent number
US06346619B1

Reaction notes

Loading…