O-Xylene → TK 12997

HRID 1462930

Reaction equation

HRID 1462930 reaction equation
C([N:4]([CH2:19][CH:20]=[CH2:21])[C:5]1[N:10]=[C:9]([N:11](CC=C)[CH2:12][CH:13]=[CH2:14])[N:8]=[C:7](Cl)[N:6]=1)C=C.[NH:22]([CH:40]1[CH2:45][C:44]([CH3:47])([CH3:46])[NH:43][C:42]([CH3:49])([CH3:48])[CH2:41]1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][CH:30]1[CH2:35][C:34]([CH3:37])([CH3:36])[NH:33][C:32]([CH3:39])([CH3:38])[CH2:31]1.[OH-].[Na+].C1(C)C(C)=C[CH:55]=[CH:56][CH:57]=1>O>[CH3:46][C:44]1([CH3:47])[CH2:45][CH:40]([N:22]([C:7]2[N:8]=[C:9]([NH:11][CH2:12][CH:13]=[CH2:14])[N:10]=[C:5]([NH:4][CH2:57][CH:56]=[CH2:55])[N:6]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]([C:7]2[N:6]=[C:5]([NH:4][CH2:19][CH:20]=[CH2:21])[N:10]=[C:9]([NH:11][CH2:12][CH:13]=[CH2:14])[N:8]=2)[CH:30]2[CH2:35][C:34]([CH3:37])([CH3:36])[NH:33][C:32]([CH3:38])([CH3:39])[CH2:31]2)[CH2:41][C:42]([CH3:49])([CH3:48])[NH:43]1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 14798Sodium HydroxideHCID 934191,6-Bis(2,2,6,6-tetramethyl-4-piperidylamino)hexaneHCID 95021s-Triazine, 2-chloro-4,6-bis(diallylamino)-

Product 1

HCID 163462TK 12997

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,4-bis(diallylamino)-6-chloro-1,3,5-triazine (14.2 grams; 0.046 mole), 4,4'-(hexamethylenediimino)bis(2,2,6,6-tetramethylpiperidine) (9.2 grams; 0.023 mole), powdered sodium hydroxide (1.84 grams; 0.046 mole), and xylene (50 mls) is heated at reflux for 36 hours using a water separator to remove byproduct water. The reaction mixture is then filtered hot and the filtrate is evaporated to obtain a light yellow oil which solidifies on standing. Recrystallization of the solid from hexane gives white needles which on recovery and drying weigh 9.3 grams, mp 119°-120° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 36 hours
  3. customto remove byproduct water
  4. filtrationThe reaction mixture is then filtered hot
  5. customthe filtrate is evaporated
  6. customto obtain a light yellow oil which
  7. customRecrystallization of the solid from hexane
  8. customgives white needles which on recovery
  9. customdrying

Sources & evidence

ORD record
ord-aebfe3aad0504efe8efca6e9b3cde66d
Source dataset
uspto-grants-1984_07
Patent number
US04461861

Linked notes

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