Thiophosgene → HCID 21509891, compound

HRID 1576762Notes

Reaction equation

HRID 1576762 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][NH:6][CH2:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:15])[CH3:2].[C:17](Cl)(Cl)=[S:18]>O1CCCC1>[CH3:14][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:8]=1[CH2:7][N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:16])[C:17](=[S:18])[NH:15]2

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 12204071HCID 12204071, compound

Product 1

HCID 21509891HCID 21509891, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of compound (10b) (15 g., 67 mmole) in 300 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere, is added 72 mmole of thiophosgene at about room temperature. Upon completion of the addition, the solution was refluxed for 10 hours, cooled to room temperature and the tetrahydrofuran removed in vacuo. The residue is dissolved in methylene chloride, washed with 5% aqueous hydrochloric acid, then water. The methylene chloride solution is dried over sodium sulfate, filtered and the solvent removed in vacuo to produce the title product.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe solution was refluxed for 10 hours
  3. customthe tetrahydrofuran removed in vacuo
  4. dissolutionThe residue is dissolved in methylene chloride
  5. washwashed with 5% aqueous hydrochloric acid
  6. dry with materialThe methylene chloride solution is dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e39d4504bacd4b59b4462867e386b083
Source dataset
uspto-grants-1976_09
Patent number
US03983120

Reaction notes

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