Acetyl chloride → HCID 178491162, compound

HRID 1934680Notes

Reaction equation

HRID 1934680 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:6][NH:7][C:8](=[O:26])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:18][C@H:19]1[CH2:24][CH2:23][C@@H:22]([OH:25])[CH2:21][CH2:20]1.C(N(CC)CC)C.[C:39](Cl)(=[O:41])[CH3:40]>ClCCl.CN(C)C1C=CN=CC=1>[C:39]([O:25][C@@H:22]1[CH2:21][CH2:20][C@H:19]([NH:18][C:10]2[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=2[C:8]([NH:7][CH2:6][C:5]2[CH:27]=[CH:28][C:29]([O:30][CH3:31])=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:26])[CH2:24][CH2:23]1)(=[O:41])[CH3:40]

Participants

6

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 178491161HCID 178491161, compound

Product 1

HCID 178491162HCID 178491162, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of N-(3,4-dimethoxybenzyl)-2-(cis-4-hydroxycyclohexylamino)-5-nitrobenzamide (1.0 g) in dichloromethane (20 mL) were added triethylamine (0.49 mL) and 4-dimethylaminopyridine (284 mg), and then acetyl chloride (0.20 mL) at 20° C. The reaction mixture was stirred for 2 hours at 20° C. and then, acetyl chloride (0.05 mL) was added. After stirring for an hour at 20° C., the reaction mixture was partitioned between chloroform and 1N-hydrochloric acid. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of ethyl acetate and hexane (1:2). The residual solid was recrystallized from ethyl acetate to give 2-[cis-4-(acetoxy)cyclohexylamino]-N-(3,4-dimethoxybenzyl)-5-nitrobenzamide (429 mg) as yellow crystals.

Workup

  1. customat 20° C
  2. stirringAfter stirring for an hour at 20° C.
  3. customthe reaction mixture was partitioned between chloroform and 1N-hydrochloric acid
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by a silica gel column chromatography
  8. washeluting with a mixture of ethyl acetate and hexane (1:2)
  9. customThe residual solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c617d819be6e4121a25f05f09924b6fa
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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