Dimethylformamide → HCID 89690029, compound

HRID 714032Notes

Reaction equation

HRID 714032 reaction equation
S(Cl)(Cl)=O.[CH2:5]([O:12][C:13]1[C:14]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[CH:15][C:16]([CH2:36][CH3:37])=[C:17]([CH:35]=1)[O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[C:24]([CH2:32][CH2:33][CH3:34])=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](O)=[O:27])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C[N:46](C=O)C.[OH-].[NH4+]>C1COCC1.O.CO>[CH2:5]([O:12][C:13]1[C:14]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[CH:15][C:16]([CH2:36][CH3:37])=[C:17]([CH:35]=1)[O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[C:24]([CH2:32][CH2:33][CH3:34])=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([NH2:46])=[O:27])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 89690113HCID 89690113, compound

Product 1

HCID 89690029HCID 89690029, compoundYield 290.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add thionyl chloride (8.22 mL, 113 mmol) dropwise to a solution of 3-[3-[5-benzyloxy-2-ethyl-4-(4-fluorophenyl)phenoxy]propoxy]-2-propyl-benzoic acid (50.0 g, 92 mmol) and DMF (2.5 mL, 32 mmol) in THF (250 mL). Stir for 1 h and then add the reaction to a solution of ammonium hydroxide (102.5 mL, 1.52 mol) at 0-5° C. Add MeOH (250 mL) and water (500 mL) in a dropwise fashion. Concentrate to about one half the volume in vacuo and stir the resulting suspension 30 min at 0-5° C. Filter the suspension on a glass frit and dry the resulting solids under vacuum to provide the title compound (50.3 g, quantitative) as an off-white solid. ES/MS m/z 542 (M+1).

Workup

  1. additionadd
  2. concentrationConcentrate to about one half the volume in vacuo
  3. stirringstir the resulting suspension 30 min at 0-5° C
  4. filtrationFilter the suspension on a glass frit
  5. customdry the resulting solids under vacuum

Sources & evidence

ORD record
ord-72362a7a26ba4437a548fb188b4edc17
Source dataset
uspto-grants-2015_11
Patent number
US09187411B2

Reaction notes

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