Thionyl Chloride → 2-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carbonyl chloride

HRID 1295348Notes

Reaction equation

HRID 1295348 reaction equation
[C:1]1([CH:7]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH2:11][CH:10]3[C:8]2([C:23]([OH:25])=O)[CH2:9]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:28])=O>CN(C=O)C.C1(C)C=CC=CC=1>[C:1]1([CH:7]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH2:11][CH:10]3[C:8]2([C:23]([Cl:28])=[O:25])[CH2:9]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 589073232-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid2×

Product 1

HCID 589073242-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carbonyl chlorideYield 101.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

To a stirring solution of racemic 2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid (1.5 g, 4.2 mmol) (Intermediate 2) and one drop DMF in 10 mL of toluene at 0° C. was added thionyl chloride (8.6 mL, 11.8 mmol). The reaction was allowed to warm to room temperature and then heated to 73° C. for 2.5 hours. The solvent and excess thionyl chloride were evaporated at reduced pressure to leave 2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carbonyl chloride (1.6 g, 100% crude yield).

Workup

  1. temperatureheated to 73° C. for 2.5 hours
  2. customThe solvent and excess thionyl chloride were evaporated at reduced pressure

Sources & evidence

ORD record
ord-fc80d2c898b8440296948e66f23d4bb4
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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