Hydrochloric Acid → HCID 178428871, compound

HRID 1640390Notes

Reaction equation

HRID 1640390 reaction equation
[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[C:17]([S:18]([CH3:20])=[O:19])=[C:16]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12].Cl.CN(C)CCCN=C=NCC.Cl.C(N(CC)CC)C.[C-]#N.[K+]>CN(C)C1C=CN=CC=1.C(Cl)Cl.CC(C)(O)C#N.C(#N)C>[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:11](=[O:12])[C:10]1[CH:14]=[CH:15][C:16]([S:21]([CH3:24])(=[O:22])=[O:23])=[C:17]([S:18]([CH3:20])=[O:19])[C:9]=1[CH3:8]

Participants

11

Reactant 6

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66738910HCID 66738910, compoundHCID 178481816HCID 178481816, compound

Product 1

HCID 178428871HCID 178428871, compound

Reagents, catalysts & solvents 4

HCID 6406Acetone CyanohydrinCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

90 mg (0.91 mmol) of 5-hydroxy-1-methylpyrazole and a spatula tip of 4-(dimethylamino)pyridine were added to 230 mg (0.83 mmol) of 2-methyl-3-methylsulfinyl-4-methylsulfonylbenzoic acid in 20 ml of CH2Cl2. 191 mg (0.99 mmol) of 1-(3′-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added, and the mixture was stirred at RT for 90 min. 3 ml of 1M HCl were then added, and the organic phase was freed from the solvent. 168 mg (1.66 mmol) of triethylamine, 10 drops of acetone cyanohydrin and a spatula tip of potassium cyanide were added to the residue in 15 ml of acetonitrile. The reaction mixture was stirred at RT for 16 h and then freed from the solvent. 15 ml of CH2Cl2 were added to the residue, and 2 ml of 1M HCl were then added. After phase separation, the organic phase was freed from the solvent. The residue was stirred with 25 ml of a mixture of aqueous saturated sodium bicarbonate solution and diethyl ether at RT for 10 min. The phases were separated, and the aqueous phase was acidified with dilute HCl and then extracted three times with CH2Cl2. The combined organic phases were freed from the solvent. This gave 171 mg of clean product.

Workup

  1. stirringThe reaction mixture was stirred at RT for 16 h
  2. additionwere then added
  3. customAfter phase separation
  4. stirringThe residue was stirred with 25 ml of a mixture of aqueous saturated sodium bicarbonate solution and diethyl ether at RT for 10 min
  5. customThe phases were separated
  6. extractionextracted three times with CH2Cl2

Sources & evidence

ORD record
ord-cdaf1d0a1fd448439dc3b5469f278c45
Source dataset
uspto-grants-2012_02
Patent number
US08114816B2

Reaction notes

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