Hydrochloric Acid → HCID 71144228, compound

HRID 2370771Notes

Reaction equation

HRID 2370771 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[Cl:13][C:14]1[CH:15]=[C:16]([CH:25]=[CH:26][C:27]=1[Cl:28])/[CH:17]=[N:18]/S(C(C)(C)C)=O.Cl>CCOCC.CO.C1COCC1>[ClH:13].[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[NH2:18])[CH:25]=[CH:26][C:27]=1[Cl:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2211262-IodopyridineHCID 87277538HCID 87277538, compoundHCID 178418339Butyllithium

Product 1

HCID 71144228HCID 71144228, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

A 250-mL round-bottomed flask was charged with 2-iodopyridine (1.0 g, 4.88 mmol) and 50 mL of THF. The resulting mixture was cooled to −100° C. and then n-BuLi (2.5 M in hexanes, 5.3 mL, 13 mmol) was added at such a rate that the internal temp did not rise above −97° C. After 15 min at −100° C., (E)-N-(3,4-dichlorobenzylidene)-2-methylpropane-2-sulfinamide (1.36 g, 4.88 mmol) was added and stirring was continued for 1 h at −100° C. 30 mL of 1M HCl in ether was added, and the mixture was allowed to warm to rt. Once at rt, 5 mL of MeOH was added and the mixture was stirred for an additional 1 h. The resulting precipitate was collected by filtration to give (3,4-dichlorophenyl)(pyridin-2-yl)-methanamine hydrochloride as a white solid.

Workup

  1. customdid not rise above −97° C
  2. waitwas continued for 1 h at −100° C
  3. temperatureto warm to rt
  4. stirringthe mixture was stirred for an additional 1 h
  5. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-d3bdddd5816c4f0eaaba2b885dddf39d
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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