4-Chlorophenol → HCID 68830312, compound

HRID 1784428Notes

Reaction equation

HRID 1784428 reaction equation
[CH3:1][O:2][C:3]1[C:4]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:5][C:6]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8][C:7]=2[CH:14]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[ClH:26].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([O:25][CH2:24][C:21]2[CH:20]=[CH:19][C:18]([S:15]([C:4]3[C:3]([O:2][CH3:1])=[CH:14][C:7]4[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=4[CH:5]=3)(=[O:17])=[O:16])=[CH:23][CH:22]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57592468HCID 57592468, compound

Product 1

HCID 68830312HCID 68830312, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-(8-methoxy-3-methyl-2,3,4,5-tetrahydro-1-H-3-benzazepine-7-sulfonyl)-phenyl]-methanol D12 (0.12 g), 4-chlorophenol (0.042 g), triphenyl phosphine (0.087 g in tetrahydrofuran (5 mL) was treated with diisopropyl azodicarboxylate (0.066 g). The solution was stirred for 18 hour then the solvent was evaporated and the residue was purified by column chromatography on silica using 0-10% methanol (containing 0.5% aqueous ammonia)-dichloromethane to give the title compound E107, which was converted to the hydrochloride salt. 1H NMR: δ CDCl3 2.36 (3H, s), 2.55 (4H, m), 2.94 (4H, m), 3.73 (3H, s), 5.08 (2H, s) 6.64 (1H, s), 6.87 (2H, d), 7.22 (2H, d), 7.50 (2H, d) 7.84 (1H, s) 7.98 (2H, d). Mass Spectrum MH+ 472

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified by column chromatography on silica using 0-10% methanol (containing 0.5% aqueous ammonia)-dichloromethane

Sources & evidence

ORD record
ord-6705e99bb3be4740825ec1a8e362f849
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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