O-Xylene → TK 12997

HRID 435220Notes

Reaction equation

HRID 435220 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-5c693575c7224b42a2410b404656f330
Source dataset
uspto-grants-1983_08
Patent number
US04400505

Reaction notes

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