Sodium Hydroxide → TK 12997

HRID 435223

Reaction equation

HRID 435223 reaction equation
[NH:1]([CH:19]1[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]1.Cl[C:30]1[N:35]=[C:34]([NH:36][C:37]([CH2:40][C:41](C)(C)C)(C)C)[N:33]=[C:32]([NH:45][C:46]([CH2:49][C:50](C)(C)C)(C)C)[N:31]=1.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:25][C:23]1([CH3:26])[CH2:24][CH:19]([N:1]([C:30]2[N:31]=[C:32]([NH:45][CH2:46][CH:49]=[CH2:50])[N:33]=[C:34]([NH:36][CH2:37][CH:40]=[CH2:41])[N:35]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([C:30]2[N:31]=[C:32]([NH:45][CH2:46][CH:49]=[CH2:50])[N:33]=[C:34]([NH:36][CH2:37][CH:40]=[CH2:41])[N:35]=2)[CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:17])([CH3:18])[CH2:10]2)[CH2:20][C:21]([CH3:28])([CH3:27])[NH:22]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 934191,6-Bis(2,2,6,6-tetramethyl-4-piperidylamino)hexaneHCID 64308146-Chloro-N,N'-(1,1,3,3-tetramethylbutyl)-[1,3,5]triazine-2,4-diamine

Product 1

HCID 163462TK 12997Yield 80.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
25 °C

Procedure

A stirred mixture of 4,4'(hexamethylenediimino)bis(2,2,6,6-tetramethylpiperidine) (6.36 grams; 0.0161 mole), 2-chloro-4,6-bis(t-octylamino)-1,3,5-triazine (9.56 grams; 0.0322 mole), and powdered sodium hydroxide (1.29 grams; 0.0322 mole) in xylene (75 mls) is stirred and heated at reflux while removing water therein by means of a water trap. The reaction mixture is stirred and heated at reflux for 18 hours, cooled to 25° C., and treated with acetonitrile (200 mls). The reaction mixture is filtered to recover a precipitate, and the solid is washed successively with water and acetone, and dried to obtain 10.0 grams of product which melts at 208°-209° C. after recrystallization from xylene.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. customwhile removing water
  4. stirringThe reaction mixture is stirred
  5. temperatureheated
  6. temperatureat reflux for 18 hours
  7. additiontreated with acetonitrile (200 mls)
  8. filtrationThe reaction mixture is filtered
  9. customto recover a precipitate
  10. washthe solid is washed successively with water and acetone
  11. customdried

Sources & evidence

ORD record
ord-ab798ed61532423db0058180fe16f7d9
Source dataset
uspto-grants-1983_08
Patent number
US04400505

Linked notes

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