Thiophosgene → HCID 178527870, compound

HRID 2352235Notes

Reaction equation

HRID 2352235 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12](Cl)(Cl)=[S:13].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]=[C:12]1[SH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 10340Sodium CarbonateHCID 77801N-Benzylethylenediamine

Product 1

HCID 178527870HCID 178527870, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Solutions of 10.9 g (0.067 mol) N-benzylethylenediamine (Example 2) and 7.65 g (0.067 mol) thiophosgene, each dissolved in 50 ml toluene, were added dropwise and concurrently to a stirred mixture of 14.1 g (0.133 mol) sodium carbonate dissolved in 100 ml water and 100 ml toluene which had been chilled to 0° C. After the 20-30 minute addition period the reaction mixture was allowed to warm to ambient temperature and stirring was continued at this temperature for one hour. The reaction mixture was filtered and the insoluble solid, 7.2 g, was recrystallized twice from methanol-ethyl acetate to give 2.25 g (18% yield) of desired product, m.p. 177°-182° C.

Workup

  1. additionAfter the 20-30 minute addition period the reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. customthe insoluble solid, 7.2 g, was recrystallized twice from methanol-ethyl acetate

Sources & evidence

ORD record
ord-555bcb67bd4645278d340426e3bc184e
Source dataset
uspto-grants-1989_10
Patent number
US04876266

Reaction notes

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