Diisopropyl Ether → 3-[N'-(acetyloxy)carbamimidoyl]phenyl acetate

HRID 1045371Notes

Reaction equation

HRID 1045371 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[NH2:4].C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20].[CH:26]([O:29]C(C)C)(C)[CH3:27]>C(Cl)Cl>[C:19]([O:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:3](=[N:2][O:1][C:26](=[O:29])[CH3:27])[NH2:4])[CH:6]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 54381771N,3-dihydroxybenzenecarboximidamide

Product 1

HCID 866633073-[N'-(acetyloxy)carbamimidoyl]phenyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 10.2 g (67 mmol) of the product obtained in Step A above in 150 ml of CH2Cl2 there are added 28 ml (0.201 mol) of triethylamine. 13.9 ml (0.147 mol) of acetic anhydride are added dropwise and the solution is stirred overnight at ambient temperature. After washing 3 times with water and then with brine, the organic phase is dried over MgSO4 and evaporated. The solid obtained is taken up in isopropyl ether and then filtered and dried to yield the title compound.

Workup

  1. washAfter washing 3 times with water
  2. dry with materialwith brine, the organic phase is dried over MgSO4
  3. customevaporated
  4. customThe solid obtained
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-df65c7fb2edb43108c94209531d66d1d
Source dataset
uspto-grants-2013_10
Patent number
US08569285B2

Reaction notes

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