1,2-Dichloroethane → HCID 13321995, compound

HRID 1262463Notes

Reaction equation

HRID 1262463 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].ClCCCl.[CH3:14][O:15][C:16]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:17]=1[C:18]([N:20]=[C:21]=[O:22])=[O:19]>C(OCC)C>[CH3:28][O:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:16]([O:15][CH3:14])[C:17]=1[C:18]([NH:20][C:21]([NH:4][C:3]1[C:2]([Cl:1])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:9])=[O:22])=[O:19]

Participants

5

Reactant 3

HCID 111,2-Dichloroethane2×HCID 118462,6-Dichloroaniline2×HCID 133219942,6-Dimethoxybenzoyl isocyanate

Product 1

HCID 13321995HCID 13321995, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 16.2 g. portion of 2,6-dichloroaniline (Aldrich Chemical Co., Milwaukee, Wis.) was dissolved in 200 ml. 1,2-dichloroethane in a flask under a nitrogen atmosphere at about 25° C. To this was added 25 g. of 2,6-dimethoxybenzoylisocyanate in 25 ml. 1,2-dichloroethane and the solution was warmed to 40° C. for two hours after the addition was complete. Thin layer chromatography on silica gel developed in diethyl ether indicated that no 2,6-dichloroaniline remained. The solvent was removed in vacuo and the residue slurried in methanol. The solids were collected and washed with methanol. Yield 26.5 g. (72%).

Workup

  1. customat about 25° C
  2. additionTo this was added 25 g
  3. additionafter the addition
  4. customThe solvent was removed in vacuo
  5. customThe solids were collected
  6. washwashed with methanol

Sources & evidence

ORD record
ord-d7d608c20975477ab7288037c60fe41f
Source dataset
uspto-grants-1984_06
Patent number
US04452631

Reaction notes

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