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Triethylamine → 4-nitro-N-methyl-N-[2-(3-phenoxycarbonylaminoprop-1-yloxy)phenyl]benzamide

HRID 323136
Notes
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Reaction equation

HRID 323136 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]([N:10]([CH3:22])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:18][CH2:19][CH2:20][NH2:21])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.Cl[C:33]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:34]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]([CH3:22])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH2:18][CH2:19][CH2:20][NH:21][C:33]([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:34])=[O:9])=[CH:23][CH:24]=1)([O-:3])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 22011031HCID 22011031, compound

Product 1

HCID 220105644-nitro-N-methyl-N-[2-(3-phenoxycarbonylaminoprop-1-yloxy)phenyl]benzamideYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-nitro-N-methyl-N-[2-(3-aminoprop-1-yloxy)phenyl]benzamide (422 mg) and triethylamine (130 mg) in dichloromethane (10 ml) was added phenyl chloroformate (201 mg) and the solution was stirred at 0° C. for 30 minutes. The reaction mixture was diluted with dichloromethane and then the organic solution was washed successively with 1N hydrochloric acid, saturated sodium bicarbonate aqueous solution and brine. Drying, filtering and removal of solvents afforded a crude product. The crude product was chromatographed on silica gel (eluent; 1% methanol in chloroform) to give 4-nitro-N-methyl-N-[2-(3-phenoxycarbonylaminoprop-1-yloxy)phenyl]benzamide (383 mg) as a slightly yellow oil.

Workup

  1. washthe organic solution was washed successively with 1N hydrochloric acid, saturated sodium bicarbonate aqueous solution and brine
  2. customDrying
  3. filtrationfiltering
  4. customremoval of solvents
  5. customafforded a crude product
  6. customThe crude product was chromatographed on silica gel (eluent; 1% methanol in chloroform)

Sources & evidence

ORD record
ord-30c77ebe71df4912a7e0547dab416dfc
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211242B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes