Hydrochloric Acid → HCID 15916793, compound

HRID 354672Notes

Reaction equation

HRID 354672 reaction equation
[NH2:1][CH2:2][CH:3]([NH:11][CH2:12][CH2:13][CH2:14][OH:15])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[C:16](=S)=[S:17].Cl>C(O)C>[F:10][C:7]1[CH:6]=[CH:5][C:4]([CH:3]2[N:11]([CH2:12][CH2:13][CH2:14][OH:15])[C:16](=[S:17])[NH:1][CH2:2]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 15916790HCID 15916790, compound

Product 1

HCID 15916793HCID 15916793, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 5.3 g of the product of Step B in 50 ml of 80% aqueous ethanol, then add 2.02 g of carbon disulfide and reflux the mixture for one (1) hour. Cool the solution then treat with 0.2 ml of concentrated hydrochloric acid and reflux the mixture for sixteen (16) hours. Concentrate the reaction mixture in vacuo, extract with methylene chloride and dry the extract. Concentrate the extract to a residue and triturate with isopropyl ether to obtain the product of this step. Yield 5.2 g M.P. 104°-106° C. Recrystallize the product from ethanol petroleum ether to obtain the product as a colorless solid. M.P. 105°-106°.

Workup

  1. temperatureCool the solution
  2. concentrationConcentrate the reaction mixture in vacuo
  3. extractionextract with methylene chloride
  4. customdry the extract
  5. concentrationConcentrate the
  6. extractionextract to a residue
  7. customtriturate with isopropyl ether
  8. customto obtain the product of this step
  9. customRecrystallize the product from ethanol petroleum ether

Sources & evidence

ORD record
ord-4d7474167fc645058f2bedbb3be1a872
Source dataset
uspto-grants-1983_03
Patent number
US04376769

Reaction notes

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