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

HRID 267743Notes

Reaction equation

HRID 267743 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 of 4,5,6,7-tetrahydrobenzo[b]-thien-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]thien-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-fac7159e66594e7faf8ffc4c7b03d24e
Source dataset
uspto-grants-1976_03
Patent number
US03944567

Reaction notes

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