Formaldehyde → HCID 54177758, compound

HRID 1388231Notes

Reaction equation

HRID 1388231 reaction equation
[NH2:1][C:2]1[C:3]([Cl:34])=[CH:4][C:5]([NH:9][C:10](=[O:33])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][S:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:20])=[O:19])=[C:6]([OH:8])[CH:7]=1.Cl[C:36](OCC)=O.[CH2:41]=[O:42].[CH3:43][NH2:44]>C(#N)C.C(O)(=O)C.O.CO>[Cl:34][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:33])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][S:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:20])=[O:19])[C:6]([OH:8])=[C:7]2[C:2]=1[NH:1][C:41](=[O:42])[N:44]([CH3:36])[CH2:43]2

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 10928Ethyl chloroformateHCID 54281195HCID 54281195, compound

Product 1

HCID 54177758HCID 54177758, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

36 g of the 5-amino-4-chloro-2-(2-dodecanesulfonamidobenzoylamino)phenol obtained in Step (ii) above was refluxed in 100 ml of acetonitrile and to the mixture was added dropwise 6.3 g of ethyl chloroformate. After refluxing for 4 hours, the reaction mixture was cooled to deposit the crystals. The crystals were collected by filtration and dried to yield 34 g thereof. 34 g of the crystals were dissolved in a solution composed of 4 ml of formalin, 8 ml of methylamine and 20 ml of methanol and the solution was refluxed for 5 hours with stirring. After the completion of the reaction, the reaction solution was cooled and poured into water. Acetic acid was added to the mixture to deposit the crystals. The crystals were collected by filtration, recrystallized from acetonitrile and dried to obtain 8.2 g of the above described coupler, having a melting point of 183° to 187° C.

Workup

  1. temperatureAfter refluxing for 4 hours
  2. temperaturethe reaction mixture was cooled
  3. filtrationThe crystals were collected by filtration
  4. customdried
  5. customto yield 34 g
  6. temperaturethe solution was refluxed for 5 hours
  7. customAfter the completion of the reaction
  8. temperaturethe reaction solution was cooled
  9. filtrationThe crystals were collected by filtration
  10. customrecrystallized from acetonitrile
  11. customdried
  12. customto obtain 8.2 g of the

Sources & evidence

ORD record
ord-e7228a99877c4591ad4ba62b9f45d391
Source dataset
uspto-grants-1984_02
Patent number
US04430423

Reaction notes

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