3,4-Dichloroaniline → 1,2-Dichloro-4-isothiocyanatobenzene

HRID 1833433Notes

Reaction equation

HRID 1833433 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[C:10](Cl)(Cl)=[S:11]>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]=[C:10]=[S:11])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 10040Thiophosgene

Product 1

HCID 230651,2-Dichloro-4-isothiocyanatobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

3,4-Dichloroaniline (19.44 g., 120 mM.) is added with vigorous stirring to a solution of thiophosgene in H2O (100 ml.) while maintaining the temperature at 15° C during the addition. The reaction is allowed to warm slowly to room temperature and is stirred for 1 hr. The aqueous layer is separated and extracted with 3 × 50 ml. CHCl3 ; the combined organic layers are dried over CaCl2 and filtered. The filtrate is evaporated in vacuo to give 3,4-dichlorophenylisothiocyanate (20.5 g.) which is used without purification in the next step.

Workup

  1. additionduring the addition
  2. temperatureto warm slowly to room temperature
  3. customThe aqueous layer is separated
  4. extractionextracted with 3 × 50 ml
  5. dry with materialthe combined organic layers are dried over CaCl2
  6. filtrationfiltered
  7. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-47dce56626174468b2dd58e59b07e635
Source dataset
uspto-grants-1978_01
Patent number
US04066681

Reaction notes

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