Thionyl Chloride → HCID 20225437, compound

HRID 1249235Notes

Reaction equation

HRID 1249235 reaction equation
[C:1]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20](O)[CH3:21])=[CH:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(Cl)([Cl:25])=O>C(Cl)Cl>[C:1]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]([Cl:25])[CH3:21])=[CH:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13749530Benzyl 3-(1-hydroxyethyl)-1H-indole-1-carboxylate

Product 1

HCID 20225437HCID 20225437, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(N-carbobenzoxy indol-3-yl)ethanol (1.02 g, 3.45 mmol) in CH2Cl2 (20 ml) at -78° C. under nitrogen was added thionyl chloride (0.63 ml, 8.62 mmol). After warming to room temperature and stirring for 2 hrs, the mixture was evaporated to a brown oil. This was dissolved in CHCl3, treated with activated carbon and filtered through a pad of Super Cel; the filtrate was evaporated to give 1.03 g (95%) of light brown oil: NMR (CDCl3) δ1.90 (3, d, CH3), 5.26 (1, q, CHCl), 5.33 (2, s, PhCH2), 7.20-7.85 (9, m, aromatic H's) 8.04 ppm (1, m, H-7). This material was relatively unstable, and therefore was used immediately without further purification (e.g. as in Example 13).

Workup

  1. customthe mixture was evaporated to a brown oil
  2. dissolutionThis was dissolved in CHCl3
  3. additiontreated with activated carbon
  4. filtrationfiltered through a pad of Super Cel
  5. customthe filtrate was evaporated
  6. customto give 1.03 g (95%) of light brown oil
  7. customwas used immediately without further purification (e.g. as in Example 13)

Sources & evidence

ORD record
ord-85480c1573d54567a0b9f19c9950b946
Source dataset
uspto-grants-1986_12
Patent number
US04629794

Reaction notes

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