Hydrochloric Acid → HCID 10657374, compound

HRID 616103Notes

Reaction equation

HRID 616103 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[N+:16]([O-])=O.Cl.C(=O)(O)[O-].[K+]>C(Cl)(Cl)Cl>[NH2:16][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:7][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 516893Potassium BicarbonateHCID 10563608HCID 10563608, compound

Product 1

HCID 10657374HCID 10657374, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.2 G. of 2-amino-4-(4-chlorophenoxy)-1-nitrobenzene in 3ml. concentrated hydrochloric acid is treated with a solution of 6 g. stannous chloride in 3 ml. concentrated hydrochloric acid. The mixture is heated briefly (about ten minutes) on a steam bath, then cooled and treated with potassium bicarbonate and chloroform. The chloroform layer is removed from the filtered mixture, dried and evaporated. 1,2-diamino-4-(4-chlorophenoxy)benzene is isolated as a gum. 1G. of 1,2-diamino-4-(4-chlorophenoxy)benzene in 20 ml. acetone is treated overnight at room temperature with 2.5 g. methoxy carbonyl isothiocyanate. The mixture is concentrated under vacuum and the residue triturated with methanol. Recrystallization from methanol gives pure 1,2-bis-(3-methoxycarbonyl-2-thioureido)-4-(4-chlorophenoxy)benzene.

Workup

  1. temperatureThe mixture is heated briefly (about ten minutes) on a steam bath
  2. temperaturecooled
  3. customThe chloroform layer is removed from the filtered mixture
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-6f991493f20e4f3f87e16c7784473abb
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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