Ethanethiol → HCID 59327676, compound

HRID 1803037Notes

Reaction equation

HRID 1803037 reaction equation
[C:1]1([P:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](O)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]([SH:25])[CH3:24].CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:17]1([P:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([S:25][CH2:23][CH3:24])=[O:11])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 12734DiisopropylcarbodiimideHCID 87021Benzoic acid, 2-(diphenylphosphino)-

Product 1

HCID 59327676HCID 59327676, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(Diphenylphosphanyl)benzoic acid (0.50 g, 1.63 mmol) and DMAP (20 mg, 0.163 mmol) were dissolved in CH2Cl2 (10 mL). Ethanethiol (EtSH, 0.35 mL, 4.89 mmol) was added, and the solution was placed under Ar(g) and cooled to 0° C. DIC (0.25 mL, 1.63 mmol) was added dropwise, and the resulting solution was allowed to warm to room temperature and stirred overnight. The solution was then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography, eluting with 10% EtOAc/hexanes, to give phosphine 1b as a pale yellow solid (0.43 g, 1.22 mmol, 75% yield).

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe solution was then filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography
  5. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-ccf93ea996324beca8facebb1d7b4a72
Source dataset
uspto-grants-2013_01
Patent number
US08350014B2

Reaction notes

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