Hydrochloric Acid → HCID 178484762, compound

HRID 1199455Notes

Reaction equation

HRID 1199455 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][N:12]=1.CNN(NC)C(Cl)=[S:23].[C:27](=[O:30])([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:11][N:12]([CH3:13])[C:27](=[S:23])[OH:30].[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2×HCID 86742401N,N-dimethylaminothiocarbamoyl chlorideHCID 135847666HCID 135847666, compound

Product 1

HCID 178484762HCID 178484762, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound from step (a) above (24.2 mmol), N,N-dimethylaminothiocarbamoyl chloride (37 mmol) in dimethyl formamide (250 ml) were stirred rapidly in the presence of potassium carbonate (60 mmol) for 24 hours, adding more potassium carbonate (1 g) after 18 hours. The mixture was acidified (to pH4) with dilute hydrochloric acid and extracted with ethyl acetate (3 times). The combined extracts were washed with water (4 times), dried (anhydrous sodium sulphate) and evaporated to yield a brown solid, which was triturated with ether, and filtered to give the sub-title compound.

Workup

  1. extractionextracted with ethyl acetate (3 times)
  2. washThe combined extracts were washed with water (4 times)
  3. dry with materialdried (anhydrous sodium sulphate)
  4. customevaporated
  5. customto yield a brown solid, which
  6. customwas triturated with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-4409e63ab65b4efba1578743707adfc3
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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