Hydrochloric Acid → HCID 178499612, compound

HRID 1685190Notes

Reaction equation

HRID 1685190 reaction equation
[CH:1]([C:13]([O:15]CC)=O)([C:8](OCC)=[O:9])[CH2:2][C:3]([O:5][CH2:6]C)=[O:4].C[O-].[Na+].Cl.[CH:22]([NH2:24])=[NH:23].Cl>CO>[OH:15][C:13]1[C:1]([CH2:2][C:3]([O:5][CH3:6])=[O:4])=[C:8]([OH:9])[N:24]=[CH:22][N:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81961Triethyl ethane-1,1,2-tricarboxylateHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 10942334Sodium Methoxide

Product 1

HCID 178499612HCID 178499612, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Add triethyl ethane-1,1,2-tricarboxylate (74.75 g; 1.00 equiv; 303.54 mmol; 69.41 mL) to a solution of sodium methoxide (139.6 mL of 25% wt in MeOH, 4.35M) (131.2 g; 2.00 equiv; 607 mmol) in methanol (224.8 mL), then add formamidine hydrochloride (25.19 g, 1.01 equiv; 306.58 mmol) at RT. Stir the mixture overnight. Acidify with 37% HCl at 0° C.; filter the solids and dry in vacuo overnight to give the title compound (55.89 g; 99.99% yield) as a white solid. 1H NMR (300 MHz, DMSO): 8.03 (s, 1H), 3.55 (s, 3H), 3.24-3.15 (m, 2H).

Workup

  1. customat RT
  2. filtrationfilter the solids
  3. customdry in vacuo overnight

Sources & evidence

ORD record
ord-ae2e676b9585405790ea8ad0cc742653
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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