1,1-Dichloroethane → HCID 20516775, compound

HRID 2199034Notes

Reaction equation

HRID 2199034 reaction equation
[NH2:1][C:2]1[C:3]([Cl:23])=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[C:21]=1[Cl:22].[C:24](Cl)(Cl)=[O:25].ClC(Cl)C>ClCCCl>[Cl:22][C:21]1[C:6]2[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])=[N:8][CH2:9][C:10](=[O:13])[N:11]([CH3:12])[C:5]=2[CH:4]=[C:3]([Cl:23])[C:2]=1[N:1]=[C:24]=[O:25]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 6371PhosgeneHCID 20516784HCID 20516784, compound

Product 1

HCID 20516775HCID 20516775, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5 g (14.25 mmol) of 7-amino-6,8-dichloro-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one are dissolved in 325 ml of 1,2-dichloroethane under reflux. The still hot solution is subsequently added dropwise while stirring and cooling with ice to 3.73 g (37.65 mmol) of phosgene in 50 ml of ice-cold 1,2-dichloroethane, the addition being carried out in such a manner that the temperature of the mixture does not exceed 20° C. The mixture is heated under reflux for 1 hour, 80 ml of dichloroethane are allowed to distill off and 80 ml of fresh dichloroethane are added thereto. While cooling with ice, argon is conducted directly into the solution until it has reached a temperature of 10° C. There is thus obtained a 1,2-dichloroethane solution of [6,8-dichloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]isocyanate.

Workup

  1. temperatureunder reflux
  2. additionThe still hot solution is subsequently added dropwise
  3. additionthe addition
  4. customdoes not exceed 20° C
  5. temperatureThe mixture is heated
  6. temperatureunder reflux for 1 hour
  7. distillationto distill off
  8. addition80 ml of fresh dichloroethane are added
  9. temperatureWhile cooling with ice, argon
  10. customa temperature of 10° C

Sources & evidence

ORD record
ord-4aee2e9be70a49acae8839d25c298d9c
Source dataset
uspto-grants-1982_11
Patent number
US04361511

Reaction notes

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