Sulfuryl chloride → HCID 57656106, compound

HRID 911219Notes

Reaction equation

HRID 911219 reaction equation
[F:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:11][CH2:12][C:6]=2[C:5]([OH:19])=[CH:4][CH:3]=1.S(Cl)([Cl:23])(=O)=O>C1(C)C=CC=CC=1.C(NC(C)C)(C)C>[Cl:23][C:4]1[CH:3]=[C:2]([F:1])[C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:16])([F:17])[F:15])[CH2:11][CH2:12][C:6]=2[C:5]=1[OH:19]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 57656514HCID 57656514, compound

Product 1

HCID 57656106HCID 57656106, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 7912DiisopropylamineCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

Dissolve 9-fluoro-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.0 g, 3.6 mmol) in toluene (36 mL) with diisopropylamine (41 μL, 0.29 mmol). Warm to 60° C. and add dropwise a solution of sulfuryl chloride (0.32 mL, 3.97 mmol) in toluene (10 mL). After 2 h, wash the mixture with brine, dry the organic layer over Na2SO4 and evaporate onto silica gel. Purify by chromatography on silica gel eluting with EtOAc/hexane (0:1 to 1:0) to obtain the desired intermediate (1.0 g, 92%). MS (ES+) m/z: 312 (M+H)+.

Workup

  1. washwash the mixture with brine
  2. dry with materialdry the organic layer over Na2SO4
  3. customevaporate onto silica gel
  4. customPurify by chromatography on silica gel eluting with EtOAc/hexane (0:1 to 1:0)

Sources & evidence

ORD record
ord-0c66b491d76a4d0cb798aeb86b06fbd2
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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