1,2-Dichloroethane → HCID 20506436, compound

HRID 354815Notes

Reaction equation

HRID 354815 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([Cl:10])=[C:4]([O:11][CH3:12])[CH:3]=1.ClCCCl.[C:17](Cl)(Cl)=[S:18].C(=O)([O-])[O-].[Ca+2]>O>[Cl:10][C:5]1[CH:6]=[C:7]([C:2]([N:1]=[C:17]=[S:18])=[CH:3][C:4]=1[O:11][CH3:12])[C:8]#[N:9]

Participants

6

Reactant 4

HCID 111,2-Dichloroethane2×HCID 10040ThiophosgeneHCID 10112Calcium CarbonateHCID 20506454HCID 20506454, compound

Product 1

HCID 20506436HCID 20506436, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 27.4 g. (0.15 mole) of 6-amino-3-chloro-4-methoxybenzonitrile in 150 ml. of 1,2-dichloro-ethane at 0°-5° C. is added with stirring a mixture of 23 g. (0.2 mole) thiophosgene, 100 ml. 1,2-dichloroethane, 20 g. (0.2 mole) calcium carbonate and 200 ml. of water. After the addition the mixture is stirred for one hour at 0°-5° C., warmed to 20° C. and stirred for 6 hours at this temperature and finally at 35° C. for an hour. The reaction mixture is filtered and the organic layer separated, washed with dilute hydrochloric acid, water and dried (MgSO4). The solvent is removed by evaporation and the residue used without purification in the next step.

Workup

  1. additiona mixture of 23 g
  2. additionAfter the addition the mixture
  3. stirringis stirred for one hour at 0°-5° C.
  4. stirringstirred for 6 hours at this temperature and finally at 35° C. for an hour
  5. filtrationThe reaction mixture is filtered
  6. customthe organic layer separated
  7. washwashed with dilute hydrochloric acid, water
  8. dry with materialdried (MgSO4)
  9. customThe solvent is removed by evaporation
  10. customthe residue used without purification in the next step

Sources & evidence

ORD record
ord-c79b6a43ac574c42b156bd90a40e9d3f
Source dataset
uspto-grants-1983_03
Patent number
US04377581

Reaction notes

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