Hydrochloric Acid → HCID 20312104, compound

HRID 2420528Notes

Reaction equation

HRID 2420528 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][C@@H:10]([C:12]([OH:14])=O)[NH2:11])=[CH:4][CH:3]=1.[O-:17][C:18]#[N:19].[K+].Cl>O.[OH-].[Na+]>[Cl:1][C:2]1[CH:16]=[C:15]2[C:5](=[CH:4][CH:3]=1)[NH:6][CH:7]=[C:8]2[CH2:9][CH:10]1[NH:11][C:18](=[O:17])[NH:19][C:12]1=[O:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6443305-ChlorotryptophanHCID 11378442Potassium cyanate

Product 1

HCID 20312104HCID 20312104, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 5-chlorotryptophan (32 g, 0.14 mole) and potassium cyanate (22.6 g, 0.28 mole) in 500 ml of H2O was heated on the steam bath for 3 hours, cooled and acidified with concentrated HCl. The solid was collected, suspended in 500 ml of 10% HCl and heated on the steam bath for 2 hours. The solid, obtained on cooling, was dissolved in dilute NaOH, filtered and acidified with dilute HCl. The solid obtained was recrystallized from aqueous 2-PrOH. Yield 17 g (37.6%), m.p. 226°-8°, contains a mole of 2-PrOH.

Workup

  1. temperaturewas heated on the steam bath for 3 hours
  2. temperaturecooled
  3. customThe solid was collected
  4. temperatureheated on the steam bath for 2 hours
  5. customThe solid, obtained
  6. temperatureon cooling
  7. filtrationfiltered
  8. customThe solid obtained
  9. customwas recrystallized from aqueous 2-PrOH

Sources & evidence

ORD record
ord-668afb10722c425b86517f96d9da4e7c
Source dataset
uspto-grants-1978_08
Patent number
US04110536

Reaction notes

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