4-Aminothiophenol → HCID 21543863, compound

HRID 2267646Notes

Reaction equation

HRID 2267646 reaction equation
[O:1]=[C:2]1[CH:8](C(OCC)=O)[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=2[NH:3]1.NC1C=CC(S)=CC=1.[Li+].[Br-]>CN(C=O)C.Cl>[C:14]1([CH:7]2[CH2:6][C:5]3[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=3[NH:3][C:2](=[O:1])[CH2:8]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 145104-AminothiophenolHCID 82050Lithium BromideHCID 68606018HCID 68606018, compound

Product 1

HCID 21543863HCID 21543863, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred slurry of ethyl 2-oxo-4-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepine-3-carboxylate (79c) (5.14 g, 16.6 mmol), 4-aminothiophenol (4.49 g, 35.9 mmol) and LiBr (8.66 g, 99.7 mmol) in 50 mL N,N′-dimethylformamide was heated to 160° C. for 24 h. The cooled mixture was diluted with 200 mL 1N HCl and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with 1N HCl, 20% K2CO3, and brine. The organic solution was dried (MgSO4), filtered, and evaporated. The crude product was triturated (EtOH/EtOAc) to give a white powder (2.96 g, 75%). 1H NMR (300 MHz, CDCl3) δ 2.55-2.72 (m, 2H), 2.90 (dd, J=7 Hz, J=14 Hz, 1H), 3.19 (dd, J=7 Hz, J=14 Hz, 1H), 3.70 (quin, J=7 Hz, 1H), 7.03 (d, J=7 Hz, 1H), 7.10-7.40 (m, 8H), 7.71 (br s, 1H). MS APCI, m/z=238 (M+1). LC/MS: 2.24 min.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined extracts were washed with 1N HCl, 20% K2CO3, and brine
  3. dry with materialThe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was triturated (EtOH/EtOAc)

Sources & evidence

ORD record
ord-014bd14e929d4c77aae1e4727b630165
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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