2-Isocyanato-1,1-dimethoxyethane → 1-Benzylidene-2-{4-[4-(4-chlorobenzoyl)benzyl]-3,5-dichlorophenyl}-4-(2,2-dimethoxy)ethyl semicarbazide

HRID 1602883Notes

Reaction equation

HRID 1602883 reaction equation
[CH:1](=[N:8][NH:9][C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:32])[C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)=[C:12]([Cl:33])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][O:35][CH:36]([O:41][CH3:42])[CH2:37][N:38]=[C:39]=[O:40]>C(#N)C>[CH:1](=[N:8][N:9]([C:10]1[CH:11]=[C:12]([Cl:33])[C:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:32])[C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)=[CH:20][CH:19]=2)=[C:14]([Cl:16])[CH:15]=1)[C:39]([NH:38][CH2:37][CH:36]([O:41][CH3:42])[O:35][CH3:34])=[O:40])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 154556412-Isocyanato-1,1-dimethoxyethaneHCID 701060661-Benzylidene-2-{4-[4-(4-chlorobenzoyl)benzyl]-3,5-dichlorophenyl}hydrazine

Product 1

HCID 541611281-Benzylidene-2-{4-[4-(4-chlorobenzoyl)benzyl]-3,5-dichlorophenyl}-4-(2,2-dimethoxy)ethyl semicarbazideYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 15 ml of acetonitrile was suspended 1.00 g of 1-benzylidene-2-{4-[4-(4-chlorobenzoyl)benzyl]-3,5-dichlorophenyl}hydrazine, and 0.40 g of 2,2-dimethoxyethyl isocyanate was added, and then 15 ml of DBU(1,8-diazabicyclo[5.4.0]undec-7-ene) was added. The mixture was reacted at 20 to 25° C. for 1 hour, and precipitated crystals were collected by filtration to give the above-identified compound as colorless crystals (yield: 75%).

Workup

  1. additionwas added
  2. customThe mixture was reacted at 20 to 25° C. for 1 hour
  3. customprecipitated crystals
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f616f2027ec748a8b45647a5e846c195
Source dataset
uspto-grants-1999_11
Patent number
US05985875

Reaction notes

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