Sulfuric Acid → HCID 13768689, compound

HRID 978804Notes

Reaction equation

HRID 978804 reaction equation
OS(O)(=O)=O.[C:6]([O:9]C(=O)C)(=O)[CH3:7].CO[CH2:15][N:16]([C:21]([CH:25]([CH3:27])[CH3:26])=[C:22]([CH3:24])[CH3:23])[C:17](=[O:20])[CH2:18][Cl:19].C(#[N:30])C>>[C:6]([NH:30][CH2:15][N:16]([C:21]([CH:25]([CH3:27])[CH3:26])=[C:22]([CH3:23])[CH3:24])[C:17](=[O:20])[CH2:18][Cl:19])(=[O:9])[CH3:7]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 13768688HCID 13768688, compound

Product 1

HCID 13768689HCID 13768689, compoundYield 48%

Procedure

To a stirred solution of 36 gm of concentrated H2SO4 at 5° C. was added 8.7 ml of acetic anhydride, and the mixture was stirred in the cold for about 0.5 hours. Acetonitrile (5.35 gm) was added, the solution was stirred for 5 minutes, and then 6.81 gm of N-methoxymethyl-2-chloro-N-[2-methyl-1-(1-methyl-ethyl)-1-propenyl]-acetamide was added. The reaction mixture was allowed to warm to room temperature over 4 hours and then partitioned between 100 ml of methylene chloride and 100 ml of H2O. The organic layer was washed with 75 ml of H2O, then 75 ml of saturated NaCl, and dried over MgSO4. Filtration and concentration gave an off-white solid which was washed through a 5 cm plug of silicagel with 50% ethyl acetate in hexane to afford 3.6 gm of product as a white solid (m.p. 113-114° C.). (48% yield) Analysis for C 12 H21ClN2O2 :

Workup

  1. stirringthe solution was stirred for 5 minutes
  2. custompartitioned between 100 ml of methylene chloride and 100 ml of H2O
  3. washThe organic layer was washed with 75 ml of H2O
  4. dry with material75 ml of saturated NaCl, and dried over MgSO4
  5. filtrationFiltration and concentration
  6. customgave an off-white solid which
  7. washwas washed through a 5 cm plug of silicagel with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-dd92566489e94078b4190bd1d3c3808f
Source dataset
uspto-grants-1987_05
Patent number
US04665228

Reaction notes

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