Hydrochloric Acid → HCID 86585535, compound

HRID 1385495Notes

Reaction equation

HRID 1385495 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:26]=[CH:25][C:6]2=[N:7][N:8]([C:10]3[CH:15]=[C:14]([C:16]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=3[OH:24])[N:9]=[C:5]2[CH:4]=1.[CH2:29]=[O:30].C([NH:35][CH2:36][CH2:37][CH2:38][CH3:39])CCC.C[O-].[Na+].Cl>>[CH2:11]([C:12]1[CH:13]=[C:14]([C:16]([CH2:19][C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:17])[CH3:18])[CH:15]=[C:10]([N:8]2[N:35]=[C:36]3[CH:37]=[CH:38][C:39]([C:2]([F:1])([F:28])[F:27])=[CH:5][C:6]3=[N:7]2)[C:29]=1[OH:30])[C:12]1[CH:13]=[C:14]([C:16]([CH2:19][C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:17])[CH3:18])[CH:15]=[C:10]([N:8]2[N:7]=[C:6]3[CH:25]=[CH:26][C:3]([C:2]([F:1])([F:27])[F:28])=[CH:4][C:5]3=[N:9]2)[C:11]=1[OH:24]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8148DibutylamineHCID 10942334Sodium MethoxideHCID 11395206HCID 11395206, compound

Product 1

HCID 86585535HCID 86585535, compoundYield 69.9%

Conditions

Temperature
160 °C

Procedure

The compound prepared in Example 31 (7.0 g, 0.018 mol), paraformaldehyde (0.29 g, 0.0093 mol) and di-n-butylamine (2.43 g, 0.0186 mol) are charged to a reaction and which is then sealed. The temperature is increased to 160° C. and held there for four hours. The reaction mass is cooled to 110° C. at which time sodium methoxide (0.16 g, 0.0028 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. Xylene is then distilled off and replaced with heptane. After cooling the heptane solution, yellow crystals separate out and are isolated by filtration. After drying to constant weight, the title compound (5 g) is obtained as a solid melting at 178° C.

Workup

  1. customis then sealed
  2. additionis added
  3. temperatureThe reaction mixture is then heated to 205° C.
  4. waitheld there for three hours
  5. temperatureThe reaction mass is then cooled to 110° C.
  6. washthe organic phase is twice washed with water
  7. distillationXylene is then distilled off
  8. temperatureAfter cooling the heptane solution, yellow crystals
  9. customseparate out
  10. customare isolated by filtration
  11. customAfter drying to constant weight

Sources & evidence

ORD record
ord-cca04f0d847f4dc48d95487ee86b5d6a
Source dataset
uspto-grants-2001_07
Patent number
US06262151B1

Reaction notes

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