Hydrochloric Acid → HCID 68452512, compound

HRID 2377056Notes

Reaction equation

HRID 2377056 reaction equation
[NH2:1][C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[ClH:12].[CH2:13]=O>O>[ClH:12].[ClH:12].[N:8]1[C:4]2[CH2:3][C@@H:2]([C:9]([OH:11])=[O:10])[NH:1][CH2:13][C:5]=2[NH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 178419078HCID 178419078, compound

Product 1

HCID 68452512HCID 68452512, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-Histidine (204.8 g, 1.32 mol) was added to water (1.2 L) and cooled in an ice/water bath. Concentrated hydrochloric acid (116.0 mL, 1.39 mol, 1.05 mol eq.) was added slowly. Formaldehyde (37 wt/wt % in water, 112.5 g, 1.39 mol, 1.05 mol eq.) was added in one portion. The reaction mixture was stirred for 30 min upon cooling with an ice/water bath, and then refluxed for 75 min. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was suspended in isopropanol (2 L) and HCl (400 mL of a 4 M solution in dioxane) for 30 min. The white solid was filtered and washed with ether. After drying in a vacuum oven (40° C.), the title product was obtained. (313.0 g, 99% yield, 95% pure). 1H NMR (DMSO-d6): 8 ppm 3.05-3.33 (m, 2H), 4.30 (s, 2H), 4.54 (m, 1H), 9.00 (s, 1H), 12.60 (br s, 3H). LCMS: Rt=0.59 min, and M+1=168.1 m/z (M+1 of free base).

Workup

  1. temperaturecooled in an ice/water bath
  2. temperatureupon cooling with an ice/water bath
  3. temperaturerefluxed for 75 min
  4. customthe solvent was removed under reduced pressure
  5. waitHCl (400 mL of a 4 M solution in dioxane) for 30 min
  6. filtrationThe white solid was filtered
  7. washwashed with ether
  8. customAfter drying in a vacuum oven (40° C.)

Sources & evidence

ORD record
ord-2799d526427a47d4bde68d9123660cb8
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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