Hydrochloric Acid → HCID 12084207, compound

HRID 1067051Notes

Reaction equation

HRID 1067051 reaction equation
[C:1]1([S:7]([C:10]2[CH:29]=[CH:28][C:13]3=[N:14][N:15]([C:17]4[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[CH:19][C:18]=4[OH:27])[N:16]=[C:12]3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:30]=[O:31].C([NH:36][CH2:37][CH2:38][CH2:39][CH3:40])CCC.C[O-].[Na+].Cl>>[CH2:18]([C:19]1[CH:20]=[C:21]([C:23]([CH3:24])([CH3:25])[CH3:26])[CH:22]=[C:17]([N:15]2[N:36]=[C:37]3[CH:38]=[CH:39][C:40]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:8])=[O:9])=[CH:12][C:13]3=[N:14]2)[C:30]=1[OH:31])[C:19]1[CH:20]=[C:21]([C:23]([CH3:26])([CH3:24])[CH3:25])[CH:22]=[C:17]([N:15]2[N:14]=[C:13]3[CH:28]=[CH:29][C:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])=[CH:11][C:12]3=[N:16]2)[C:18]=1[OH:27]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8148DibutylamineHCID 10942334Sodium MethoxideHCID 12084214HCID 12084214, compound

Product 1

HCID 12084207HCID 12084207, compoundYield 54.3%

Conditions

Temperature
205 °C

Procedure

5-Phenylsulfonyl-2-(2-hydroxy-5-tert-butylphenyl)-2H-benzotriazole (15 g, 0.037 mol), paraformaldehyde (0.63 g, 0.019 mol) and di-n-butylamine (5.0 g, 0.386 mol) are charged to a reactor which is then sealed. The temperature is increased to 110° C. at which time sodium methoxide (0.33 g, 0.0069 mol) is added. The reaction mixture is then heated to 205° C. and held there for three hours, The reaction mass is then cooled to 110° C. and 100 mL of xylenes are added. The reaction mass is neutralized with 10% aqueous hydrochloric acid and the organic phase is twice washed with water. The xylene phase is filtered through a plug of silica gel and is then distilled. The crude Mannich product is recrystallized twice from heptane to yield 8.3 g of the title compound having a melting point of 224-234° C.

Workup

  1. customis then sealed
  2. additionis added
  3. temperatureThe reaction mass is then cooled to 110° C.
  4. washthe organic phase is twice washed with water
  5. filtrationThe xylene phase is filtered through a plug of silica gel
  6. distillationis then distilled
  7. customThe crude Mannich product is recrystallized twice from heptane

Sources & evidence

ORD record
ord-c07b22b704d1465b9335e6ee35160680
Source dataset
uspto-grants-2001_06
Patent number
US06245915B1

Reaction notes

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