Hydrochloric Acid → HCID 178419939, compound

HRID 2273048Notes

Reaction equation

HRID 2273048 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[N:17]=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]3[CH2:32][CH2:31][CH:30]([C:33]4[N:34]=[C:35]([C@@H:38]5[CH2:42][CH2:41][CH2:40][N:39]5C(OCC5C=CC=CC=5)=O)[NH:36][CH:37]=4)[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[NH:19][CH:20]=1)=O)C1C=CC=CC=1.C(Cl)(=O)C.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl.C(OCC)(=O)C>[NH:39]1[CH2:40][CH2:41][CH2:42][C@H:38]1[C:35]1[NH:36][CH:37]=[C:33]([CH:30]2[CH2:31][CH2:32][CH:27]([C:24]3[CH:25]=[CH:26][C:21]([C:18]4[NH:19][CH:20]=[C:16]([C@@H:12]5[CH2:13][CH2:14][CH2:15][NH:11]5)[N:17]=4)=[CH:22][CH:23]=3)[CH2:28][CH2:29]2)[N:34]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178525132HCID 178525132, compound

Product 1

HCID 178419939HCID 178419939, compoundYield 202.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of A5 (19.2 g) in dichloromethane (500 mL) at −20° C. was added acetyl chloride (16.8 mL), followed by aluminum chloride (43 g). The reaction was allowed to warm up to rt. After overnight stirring, the reaction was poured into a mixture of ethyl acetate (800 mL), 1M HCl (800 mL) along with some ice. After separating the organic layer, the aqueous layer was extracted with ethyl acetate (3×300 mL). The combined organic layers were washed with brine, H2O, dried over Na2SO4, filtered, and concentrated to afford A6 (24 g), which was used for next reaction without further purification.

Workup

  1. customAfter separating the organic layer
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×300 mL)
  3. washThe combined organic layers were washed with brine, H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-35cb74e2b05d4d7e8ba51a884625b570
Source dataset
uspto-grants-2015_09
Patent number
US09120779B2

Reaction notes

Loading…