Methanol → HCID 22010658, compound

HRID 323178Notes

Reaction equation

HRID 323178 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:37]=[CH:36][C:20]([C:21]([N:23]([CH3:35])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33]O)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:58].CO>ClCCl.C(OCC)(=O)C.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:37]=[CH:36][C:20]([C:21]([N:23]([CH3:35])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][Br:58])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22010692HCID 22010692, compound

Product 1

HCID 22010658HCID 22010658, compoundYield 92.1%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(3-hydroxypropoxy)phenyl]benzamide (520 mg) in dichloromethane (20 ml) was added triphenylphosphine (827 mg) and carbon tetrabromide (1.39 g) at ambient temperature. The mixture was stirred for 2 hours and diluted with ethyl acetate and washed successively with saturated sodium hydrogen carbonate and brine, and dried over magnesium sulfate. The solid was removed and the solvent was removed by evaporation to give crude product. The crude material was subjected to a silica gel column chromatography (SiO2; 50 g, 0.5% methanol in chloroform) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(3-bromopropoxy)phenyl]benzamide (540 mg) as white amorphous.

Workup

  1. washwashed successively with saturated sodium hydrogen carbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solid was removed
  4. customthe solvent was removed by evaporation
  5. customto give crude product

Sources & evidence

ORD record
ord-5283998ff2e04f658d8a935b02749ab8
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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