Hydrochloric Acid → HCID 13766010, compound

HRID 543283Notes

Reaction equation

HRID 543283 reaction equation
CN(C)C=O.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:10][C:11]1[S:12][C:13]([Cl:17])=[CH:14][C:15]=1[NH-:16].C1(=O)N([O:23][C:24]([C:26]2[C:30]([C:31](O)=[O:32])=[CH:29][S:28][CH:27]=2)=O)C(=O)CC1.Cl>>[Cl:17][C:13]1[S:12][C:11]([Cl:10])=[C:15]2[C:14]=1[C:24](=[O:23])[C:26]1=[CH:27][S:28][CH:29]=[C:30]1[C:31](=[O:32])[NH:16]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6451240Aluminum(III) ChlorideHCID 86741460HCID 86741460, compound

Product 1

HCID 13766010HCID 13766010, compoundYield 94.2%

Procedure

109.5 g (116 ml; 1.50 moles) of dimethylformamide were added to 798 g (5.98 moles) of anhydrous aluminum chloride in the course of 15 minutes, while stirring, a highly exothermic reaction taking place. Thereafter, 250 g (0.596 mole) of thiophene-3,4-dicarboxylic acid succinimido ester [N-(2,5-dichlorothien-3-yl)]-amide were added to the stirred mixture at 80° C. in the course of 30 minutes. The reaction mixture was stirred for a further 3 hours at this temperature and then poured, in the warm state and while stirring, onto 4.5 kg of ice and 470 ml (561.2 g; 5.85 moles) of concentrated hydrochloric acid. The crystals precipitated during this procedure were filtered off under suction, washed in succession with 6 l of water, with twice 0.5 l of acetone and with twice 0.5 l of petroleum ether (boiling range 40°-60° C.) and dried at 50° C. in a drying oven under reduced pressure. 170.8 g (94%) of 1,3dichloro-4,5-dihydrodithieno[3,4-b:3',4'-e]azepine-5,9-dione were isolated in the form of beige crystals of melting point 236.5°-239° C.

Workup

  1. customa highly exothermic reaction
  2. stirringThe reaction mixture was stirred for a further 3 hours at this temperature
  3. additionpoured, in the warm state
  4. customThe crystals precipitated during this procedure
  5. filtrationwere filtered off under suction
  6. washwashed in succession with 6 l of water, with twice 0.5 l of acetone and with twice 0.5 l of petroleum ether (boiling range 40°-60° C.)
  7. customdried at 50° C. in a drying oven under reduced pressure

Sources & evidence

ORD record
ord-dac9a11dfcbd4f31898d46e4baab678c
Source dataset
uspto-grants-1987_04
Patent number
US04661591

Reaction notes

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