Ammonia → HCID 178512121, compound

HRID 1833404Notes

Reaction equation

HRID 1833404 reaction equation
[NH2:1][CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1.[Cl:12][C:13]([Cl:18])([Cl:17])[C:14](Cl)=O.P(Cl)(Cl)(Cl)(Cl)Cl.Cl.[N:26]1C=CC=CC=1.N>O.C1C=CC=CC=1>[NH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([CH2:2][NH:1][C:14](=[NH:26])[C:13]([Cl:18])([Cl:17])[Cl:12])=[CH:4]1

Participants

9

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 24819Phosphorus pentachlorideHCID 4721071H-Indol-3-Ylmethanamine

Product 1

HCID 178512121HCID 178512121, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 14.6 g. (0.1 mole) of 3-(aminomethyl) indole in 30 ml. of benzene is added dropwise 18.2 g. (0.1 mole) of trichloroacetyl chloride over a period of approximately 5 minutes. The reaction mixture is heated at reflux for 30 minutes, cooled and concentrated to dryness in vacuo. The resultant solid is broken up and ground in a mortar to give a powder which is mixed well with 20.8 g. (0.1 mole) of phosphorus pentachloride. The mixture is heated in an oil bath at 110° C. until the evolution of hydrogen chloride ceases (approximately 3 hours). The reaction mixture containing the imidoyl chloride is cooled to room temperature and dry pyridine (7.9 g., 0.1 mole) is added followed by 6.5 ml. of concentrated aqueous ammonia. The reaction mixture is then stirred and warmed to 90° C. for 30 minutes, after which 100 ml. of water is added dropwise to precipitate the product. Overnight storage in the cold affords a solid which is crystallized from benzene-hexane to provide N-(3-indolylmethyl) trichloroacetamidine m.p. 135.5° to 138.5° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 30 minutes
  3. temperaturecooled
  4. concentrationconcentrated to dryness in vacuo
  5. customto give a powder which
  6. additionis mixed well with 20.8 g
  7. temperaturewarmed to 90° C. for 30 minutes
  8. customto precipitate the product
  9. customOvernight storage in the cold affords a solid which
  10. customis crystallized from benzene-hexane

Sources & evidence

ORD record
ord-f613ef762cb14110b5c7c71ca084edb4
Source dataset
uspto-grants-1978_01
Patent number
US04066661

Reaction notes

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