Chloroform → 2-Chloro-4,5,6,7-tetrahydro-1-benzothiophen-4-amine

HRID 259325Notes

Reaction equation

HRID 259325 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][C:4]2[CH:7]([NH2:11])[CH2:8][CH2:9][CH2:10][C:3]1=2.C(Cl)(Cl)[Cl:13].S(Cl)(Cl)(=O)=O.[OH-].[Na+]>O>[Cl:13][C:6]1[S:2][C:3]2[CH2:10][CH2:9][CH2:8][CH:7]([NH2:11])[C:4]=2[CH:5]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 173886004,5,6,7-Tetrahydrobenzo[b]thiophen-4-amine hydrochloride

Product 1

HCID 203489752-Chloro-4,5,6,7-tetrahydro-1-benzothiophen-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of 11.4 grams 4,5,6,7-tetrahydrobenzo[b]-thiophen-4-amine hydrochloride is stirred in 150 ml. of chloroform at about 10° C., and 6.1 ml. of sulfuryl chloride is added dropwise. The mixture is stirred for 3.5 hours at room temperature, and then about 20 ml. of 50% sodium hydroxide solution is added gradually to dissolve the suspended solid. The mixture is then poured into water and extracted with chloroform twice. The extracts are dried, evaporated to dryness, and the residue is distilled to give 7.4 grams of 2-chloro-4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine, boiling point 94° C. to 98° C./0.5 Torr.

Workup

  1. customat about 10° C.
  2. dissolutionto dissolve the suspended solid
  3. extractionextracted with chloroform twice
  4. customThe extracts are dried
  5. customevaporated to dryness
  6. distillationthe residue is distilled

Sources & evidence

ORD record
ord-4802d0711a464bb9b91b2959a8da4a05
Source dataset
uspto-grants-1977_07
Patent number
US04036979

Reaction notes

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