Hydrochloric Acid → HCID 21904380, compound

HRID 1839228Notes

Reaction equation

HRID 1839228 reaction equation
[Zn](CC)[CH2:2]C.C(I)I.[CH2:9]([N:16]1[CH2:21][CH2:20][CH:19]=[C:18]([CH2:22][OH:23])[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>C(Cl)Cl>[CH2:9]([N:16]1[CH2:21][CH2:20][CH:19]2[C:18]([CH2:22][OH:23])([CH2:2]2)[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6346DiiodomethaneHCID 21904425HCID 21904425, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 21904380HCID 21904380, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ZnEt2 (17.3 ml, 1.0 M) in CH2Cl2 (20 ml) at 0° C. was added CH2I2 (1.4 ml) (CAUTION: exothermic!). After stirring for 15 min, a solution of 172 (352 mg, 1.73 mmol) in CH2Cl2 (2 ml) was added. The mixture was stirred from 0° C. to room temperature overnight. 5% HCl was added to bring the mixture to a homogeneous solution. (white solid dissolved). The two layers were separated. Aqueous layer was neutralized with 2N KOH to pH=10-12, extracted with CH2Cl2 (twice). The combined organic solution was dried (K2CO3/NaSO4), filtered and concentrated. The LRMS of the crude mixture showed that the ratio of 173 to 172 was about 1:1. The product was not isolated from the starting material due to their similar polarities. LRMS (calculated for C14H19NO) 217, found 217.

Workup

  1. stirringThe mixture was stirred from 0° C. to room temperature overnight
  2. dissolution(white solid dissolved)
  3. customThe two layers were separated
  4. extractionextracted with CH2Cl2 (twice)
  5. dry with materialThe combined organic solution was dried (K2CO3/NaSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was not isolated from the starting material due to their similar polarities

Sources & evidence

ORD record
ord-25a32d7165db46448c38b062a6851670
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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