Oxalyl chloride → HCID 11974449, compound

HRID 1373267Notes

Reaction equation

HRID 1373267 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:14]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=1)[NH2:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:25](Cl)(=[O:29])[C:26](Cl)=[O:27]>CO>[CH2:2]([O:9][C:10]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[C:12]2[C:11]=1[C:25](=[O:29])[C:26](=[O:27])[NH:13]2)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 122173163,5-dibenzyloxyaniline hydrochloride

Product 1

HCID 11974449HCID 11974449, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 3,5-dibenzyloxyaniline hydrochloride (J. Org. Chem., 1975, 40, 1556; 10 g) and oxalyl chloride (15 ml) was heated to 170° C. for 3 hours. The mixture was cooled to ambient temperature, methanol (45 ml) was added and the mixture was heated to reflux for 1 hour. The mixture was cooled to ambient temperature and the precipitate was isolated, washed with methanol and dried under vacuum to give 4,6-dibenzyloxy-2,3-dioxoindoline (8.8 g); NMR Spectrum: (DMSOd6) 5.22 (s, 2H), 5.28 (s, 2H), 6.12 (s, 1H), 6.42 (s, 1H), 7.3–7.55 (m, 10H), 10.97 (s, 1H).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1 hour
  4. temperatureThe mixture was cooled to ambient temperature
  5. customthe precipitate was isolated
  6. washwashed with methanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-b20f8f5d1f5f47dcb9461757861face0
Source dataset
uspto-grants-2007_01
Patent number
US07160891B2

Reaction notes

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