Ammonium Chloride → HCID 58477511, compound

HRID 474210Notes

Reaction equation

HRID 474210 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[N:20]=[CH:19][C:18](B4OC(C)(C)C(C)(C)O4)=[CH:17][N:16]=3)[CH:10]=2)[N:6]=[C:5]([C:30]2[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=2)[C:33]#[N:34])[CH:4]=[CH:3]1.B1([O-])O[O:39]1.O.O.O.O.[Na+].[Cl-].[NH4+]>C1COCC1.O.ClCCl>[OH:39][C:18]1[CH:17]=[N:16][C:15]([C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[CH2:8][N:7]2[C:2](=[O:1])[CH:3]=[CH:4][C:5]([C:30]3[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=3)[C:33]#[N:34])=[N:6]2)=[N:20][CH:19]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 58477513HCID 58477513, compound

Product 1

HCID 58477511HCID 58477511, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

50.46 g of 3-(6-oxo-1-{3-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrimidin-2-yl]benzyl}-1,6-dihydropyridazin-3-yl)benzonitrile (102.7 mmol) and 33.81 g of sodium perborate tetrahydrate (339 mmol) in a mixture of 220 ml of THF and 220 ml of water are mixed in a 1000 ml one-necked flask and stirred at room temperature for 2 h, during which a pale precipitate deposits. The reaction mixture is diluted with 800 ml of dichloromethane, shaken with 500 ml of saturated aqueous ammonium chloride solution, dried over sodium sulfate and evaporated to dryness in a rotary evaporator. The residue is slurried in methanol, filtered off with suction and washed with diethyl ether, m.p. 245-8° C.

Workup

  1. additionare mixed in a 1000 ml one-necked flask
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness in a rotary evaporator
  4. filtrationfiltered off with suction
  5. washwashed with diethyl ether, m.p. 245-8° C.

Sources & evidence

ORD record
ord-eb2b5369770b4208a502ce76609a86d8
Source dataset
uspto-grants-2014_01
Patent number
US08637518B2

Reaction notes

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