Hydrochloric Acid → HCID 178477613, compound

HRID 1640389Notes

Reaction equation

HRID 1640389 reaction equation
[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[CH:3]=1.[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[C:12]([CH3:19])[C:11]=1[S:20]([CH2:22][CH3:23])=[O:21].Cl.CN(C)CCCN=C=NCC.Cl.C(N(CC)CC)C.[C-]#N.[K+].C(=O)(O)[O-].[Na+]>ClCCl.CC(C)(O)C#N.C(#N)C.C(OCC)C>[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([C:3]2[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=2[OH:1])=[O:15])=[C:12]([CH3:19])[C:11]=1[S:20]([CH2:22][CH3:23])=[O:21]

Participants

12

Reactant 7

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66738909HCID 66738909, compoundHCID 178429390HCID 178429390, compound

Product 1

HCID 178477613HCID 178477613, compound

Reagents, catalysts & solvents 4

HCID 6406Acetone CyanohydrinCatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

128 mg (1.14 mmol) of 5-hydroxy-1,3-dimethylpyrazole were added to 270 mg (purity 95% by weight; 1.04 mmol) of 4-chloro-3-ethylsulfinyl-2-methylbenzoic acid in 20 ml of dichloromethane (CH2Cl2). 239 mg (1.24 mmol) of 1-(3′-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added, and the mixture was stirred at RT for 16 h. For work-up, 3 ml of 1M HCl were added, and the organic phase was freed from the solvent. 210 mg (2.07 mmol) of triethylamine, 10 drops of acetone cyanohydrin and a spatula tip of potassium cyanide were added to the residue in 20 ml of acetonitrile. The reaction mixture was stirred at RT for 16 h and then freed from the solvent. The residue was stirred at RT with 25 ml of a mixture of aqueous saturated sodium bicarbonate solution and diethyl ether for 10 min. The phases were separated, and the aqueous phase was acidified with dilute HCl and then extracted with CH2Cl2. The organic phase was freed from the solvent and the residue was then purified chromatographically. This gave 100 mg of clean product.

Workup

  1. stirringThe reaction mixture was stirred at RT for 16 h
  2. customThe phases were separated
  3. extractionextracted with CH2Cl2
  4. customthe residue was then purified chromatographically

Sources & evidence

ORD record
ord-e20a6497e3d745b0bdf0ba47cc0e47f8
Source dataset
uspto-grants-2012_02
Patent number
US08114816B2

Reaction notes

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