Ammonia → HCID 21444097, compound

HRID 328143Notes

Reaction equation

HRID 328143 reaction equation
[Cl:1][C:2]1[C:3]([C:24](O)=[O:25])=[C:4]([C:18]([Cl:23])=[C:19]([Cl:22])[C:20]=1[Cl:21])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][CH:8]=1)=[O:6].[CH2:27]([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]3[CH:41]=[CH:40][CH:39]=[CH:38][C:36]3=2)[CH:31]=[C:30]1[CH3:42])[CH3:28].N>C(OC(=O)C)(=O)C>[CH2:14]([N:13]([CH2:16][CH3:17])[C:10]1[CH:9]=[CH:8][C:7]([C:5]2([C:31]3[C:32]4[C:37](=[C:36]5[CH:38]=[CH:39][CH:40]=[CH:41][C:35]5=[CH:34][CH:33]=4)[N:29]([CH2:27][CH3:28])[C:30]=3[CH3:42])[C:4]3[C:3](=[C:2]([Cl:1])[C:20]([Cl:21])=[C:19]([Cl:22])[C:18]=3[Cl:23])[C:24](=[O:25])[O:6]2)=[CH:12][CH:11]=1)[CH3:15]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 151143961-Ethyl-2-methyl-1H-benzo[G]indoleHCID 199566113,4,5,6-Tetrachloro-2-carboxy-4'-diethylaminobenzophenone

Product 1

HCID 21444097HCID 21444097, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of about 6.5 grams of 3,4,5,6-tetrachloro-2-carboxy-4'-diethylaminobenzophenone and about 3.1 grams of 1-ethyl-2-methyl-1H-benz[g]indole in 50 milliliters of acetic anhydride is refluxed for about one hour and then cooled. That reaction mixture is poured over ice and ammonia, extracted twice with a 1:1 toluene-chloroform mixture and dried using sodium sulfate. The solution is concentrated by evaporation of the solvent and the title compound is crystallized by washing with petroleum ether. 9.3 grams of the title compound is obtained having a melting point of 232°-235° C. A solution of product imparts a blue color to paper coated with a phenolic resin or silton clay or a combination of the two. The calculated analysis for C33H28N2O2Cl4, the title compound, is C, 63.28%; H, 4.51%; N, 4.57%; and Cl, 22.64%. Found, on analysis: C, 63.37%; H, 4.42%; N, 4.54%; an Cl, 22.49%.

Workup

  1. temperaturecooled
  2. extractionextracted twice with a 1:1 toluene-chloroform mixture
  3. customdried
  4. concentrationThe solution is concentrated by evaporation of the solvent
  5. customthe title compound is crystallized
  6. washby washing with petroleum ether

Sources & evidence

ORD record
ord-b96c5ea8d45749c1befd534efb360883
Source dataset
uspto-grants-1977_04
Patent number
US04016174

Reaction notes

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