Hydrochloric Acid → HCID 87126409, compound

HRID 1042095Notes

Reaction equation

HRID 1042095 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:10]=1[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[N:28]([O-])=O.[Na+].[CH3:32][CH:33](C(=O)C)[C:34]([O:36][CH2:37][CH3:38])=[O:35].[OH-].[K+]>O.C(O)C.C(#N)C>[CH2:1]([O:8][C:9]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:10]=1[NH:11]/[N:28]=[C:33](\[CH3:32])/[C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 701Ethyl 2-methylacetoacetateHCID 14797Potassium HydroxideHCID 23668193Sodium NitriteHCID 46941671HCID 46941671, compound

Product 1

HCID 87126409HCID 87126409, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent3×HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Conditions

Temperature
-5 °C

Procedure

2-(Benzyloxy)-4-[4-(methylsulfonyl)phenoxy]aniline (43.8 g) was suspended in a mixed solvent of acetonitrile(50 mL)-ethanol (400 mL), and concentrated hydrochloric acid (25 mL) was added at 10° C. Moreover, ethanol (100 mL) was added. Sodium nitrite (9.8 g) dissolved in water (16 mL) was added dropwise at −5 to 0° C., and the mixture was stirred at −5° C. for 30 min. To the reaction mixture was added water (100 mL), and the mixture was added dropwise to a mixture of ethyl 2-methyl-3-oxobutanoate (18.8 mL), potassium hydroxide (85%, 23 g), water (100 mL), and ethanol (100 mL) at −13 to −11° C. over 2 hr. The reaction mixture was stirred at −11° C. for 40 min, and the precipitated orange solid was collected by filtration. The obtained solid was washed with ethanol and diethyl ether to give the title compound (52.3 g, yield 91%) as orange crystals.

Workup

  1. additionwas added at 10° C
  2. additionwas added dropwise at −5 to 0° C.
  3. stirringThe reaction mixture was stirred at −11° C. for 40 min
  4. filtrationthe precipitated orange solid was collected by filtration
  5. washThe obtained solid was washed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-8888e4ff079e41a0b3a3830b10587bd3
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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