Sodium Bicarbonate → HCID 58026184, compound

HRID 1514356Notes

Reaction equation

HRID 1514356 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]([C:10]1[N:15]=[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH:13]=[C:12]([CH3:24])[N:11]=1)[NH:6]C(=O)C.C(=O)([O-])O.[Na+]>Cl.O>[Br:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]([C:10]1[N:15]=[C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[CH:13]=[C:12]([CH3:24])[N:11]=1)[NH2:6]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 58026186HCID 58026186, compound

Product 1

HCID 58026184HCID 58026184, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Acetic acid N′-(2-bromo-benzyl)-N′-[4-(4-chloro-phenylamino)-6-methyl-pyrimidin-2-yl]-hydrazide (0.4 g, 0.87 mmol) was suspended in aqueous hydrochloric acid (6 M, 50 mL) and heated to 100° C. for 3 days. The reaction mixture was diluted with water (50 mL), basified with solid sodium hydrogencarbonate and extracted with chloroform (3×50 mL). The combined organic phases were washed with brine, dried over sodium sulphate, filtrated and evaporated to give {2-[N-(2-bromo-benzyl)-hydrazino]-6-methyl-pyrimidin-4-yl}-(4-chloro-phenyl)-amine (0.3 g, 82%) as a brown solid.

Workup

  1. extractionextracted with chloroform (3×50 mL)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-8c5c7abb2ee142f08423fbd016a6e764
Source dataset
uspto-grants-2012_07
Patent number
US08222262B2

Reaction notes

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