Thionyl Chloride → 4-(Aminosulfonyl)-3-thiophenecarbonyl chloride

HRID 1731409Notes

Reaction equation

HRID 1731409 reaction equation
[NH2:1][S:2]([C:5]1[C:6]([C:10]([OH:12])=O)=[CH:7][S:8][CH:9]=1)(=[O:4])=[O:3].S(Cl)([Cl:15])=O>>[NH2:1][S:2]([C:5]1[C:6]([C:10]([Cl:15])=[O:12])=[CH:7][S:8][CH:9]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 30422853-Thiophenecarboxylic acid, 4-(aminosulfonyl)-

Product 1

HCID 137325564-(Aminosulfonyl)-3-thiophenecarbonyl chloride

Procedure

A mixture of 1 g. of 4-(aminosulfonyl)-3-thiophenecarboxylic acid in 20 ml of thionyl chloride is heated under reflux for 4 hours. The mixture is cooled to room temperature and is filtered. The filtrate is evaporated in a rotary evaporator and the residue is dissolved in 270 ml. of anhydrous ether. The solution is diluted with 200 ml. of petroleum ether and the precipitate which forms is collected to give 0.4 g. of product, m.p. 140; 262°-265° C.; mass spectrum CI m/e 226 MH+.

Workup

  1. additionA mixture of 1 g
  2. temperatureunder reflux for 4 hours
  3. filtrationis filtered
  4. customThe filtrate is evaporated in a rotary evaporator
  5. dissolutionthe residue is dissolved in 270 ml
  6. additionThe solution is diluted with 200 ml
  7. customof petroleum ether and the precipitate which forms is collected
  8. customto give 0.4 g
  9. custom262°-265° C.

Sources & evidence

ORD record
ord-940f34b62c524172b0972cfe1d4a3083
Source dataset
uspto-grants-1986_11
Patent number
US04621142

Reaction notes

Loading…