Acetic Anhydride → Acetamidomalonic acid diethyl ester

HRID 526287Notes

Reaction equation

HRID 526287 reaction equation
Cl.[NH2:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[C:21](OC(=O)C)(=[O:23])[CH3:22]>ClCCl>[C:21]([NH:2][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 14041Acetamidomalonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternatively, diethyl 2-aminomalonate hydrochloride (21.4 g, 100 mmol) and triethylamine (56 mL, 400 mmol, 4.0 eq.) were dissolved in dichloromethane (500 mL) and stirred with acetic anhydride (9.5 mL, 100 mmol, 1.0 eq.) at 0° C. and overnight at r.t. The mixture was washed with brine (2×200 mL) and dried over MgSO4. The organic phase was filtered through a short silica gel column I (6×6 cm, dichloromethane). The product 1 was isolated as a white crystalline solid. Yield: 22.08 g (100%); 99% purity (GC).

Workup

  1. washThe mixture was washed with brine (2×200 mL)
  2. dry with materialdried over MgSO4
  3. filtrationThe organic phase was filtered through a short silica gel column I (6×6 cm, dichloromethane)

Sources & evidence

ORD record
ord-cb8510ed29ac4d47abfd41ea423a479c
Source dataset
uspto-grants-2016_05
Patent number
US09345791B2

Reaction notes

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