(Chlorothio)formyl chloride → HCID 69438128, compound

HRID 404928Notes

Reaction equation

HRID 404928 reaction equation
[CH:1]([O:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[S:11][C:12]([C:15]([NH2:17])=[O:16])=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Cl[C:21]([S:23]Cl)=[O:22]>C1(C)C=CC=CC=1>[CH:1]([O:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[O:16][C:21](=[O:22])[S:23][N:17]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 69436463HCID 69436463, compound

Product 1

HCID 69438128HCID 69438128, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of Example 100A (1.89 g, 0.0066 mol) and chlorocarbonylsulfenyl chloride (0.64 g, 0.01 mol) in toluene was heated at reflux for 6 hours. The solvent was removed and the residue was purified on silica gel (5˜30% ethyl acetate in hexane) to give 2.05 g of product as an off-white solid (92% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (d, J=6.25 Hz, 6H) 4.46-4.63 (m, 1H) 6.89-6.98 (m, 2H) 7.14-7.24 (m, 2H) 7.80 (s, 1H). MS (ESI), M/Z: 369.0 (M+32)+.

Workup

  1. temperatureat reflux for 6 hours
  2. customThe solvent was removed
  3. customthe residue was purified on silica gel (5˜30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ce025163c99c4be3a969c4255c4aa4e0
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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