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Isobutyl nitrite → Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-chlorophenyl)acetate

HRID 1927731
Notes
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Reaction equation

HRID 1927731 reaction equation
N(OCC(C)C)=O.[Cl:8][C:9]1[CH:39]=[CH:38][C:12]([CH2:13][CH2:14][NH:15][C:16]([C:18]2[CH:36]=[CH:35][C:21]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:25][C:24]=3[Cl:34])=[C:20](N)[CH:19]=2)=[O:17])=[CH:11][CH:10]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][CH2:14][NH:15][C:16]([C:18]2[CH:36]=[CH:35][C:21]([O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:25][C:24]=3[Cl:34])=[CH:20][CH:19]=2)=[O:17])=[CH:38][CH:39]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 10958Isobutyl nitriteHCID 68467172Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-aminophenoxy)-3-chlorophenyl)acetate

Product 1

HCID 68466220Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-chlorophenyl)acetateYield 72.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
60 °C

Procedure

Isobutyl nitrite (0.0751 ml, 0.634 mmol) was diluted with DMF (1 mL), placed under nitrogen and heated to 60° C. Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)-2-aminophenoxy)-3-chlorophenyl)acetate (100 mg, 0.211 mmol) in DMF (1 mL) was added dropwise and the reaction was stirred for 1 hour. The reaction was cooled, diluted with ethyl acetate and washed with 2N HCl, saturated sodium bicarbonate and brine. The organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a biotage 12i column, eluting with DCM:MeOH (99:1) to yield methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-chlorophenyl)acetate (70 mg, 72.3% yield).

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with 2N HCl, saturated sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was purified
  7. washeluting with DCM:MeOH (99:1)

Sources & evidence

ORD record
ord-930983b26de04890a31a4bd6af2cfe98
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08183289B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes