Ammonia → HCID 21293088, compound

HRID 622385Notes

Reaction equation

HRID 622385 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.CO[C:15]1[C:19](OC)=[N:18][S:17](=[O:22])[N:16]=1.[NH3:23]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:15]2[C:19]([NH2:23])=[N:18][S:17](=[O:22])[N:16]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 107281442-N-(3-Aminopropyl)-amino-5-bromopyridineHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxide

Product 1

HCID 21293088HCID 21293088, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3-(5-bromopyrid-2-ylamino)propylamine (1 g) and 3,4-dimethoxy-1,2,5-thiadiazole-1-oxide (0.71 g) was stirred in methanol for 3 hours. Methanol saturated with ammonia (10 ml) was added and the solution was stirred for 18 hours, concentrated in vacuo and the residue was chromatographed on silica eluted with 10% v:v methanol in chloroform followed by recrystallisation from methanol to give 3-[3-(5-bromopyrid-2-ylamino)propylamino]-4-amino-1,2,5-thiadiazole-1-oxide (0.63 g), m.p. 215°-216° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was chromatographed on silica
  3. washeluted with 10% v
  4. customv methanol in chloroform followed by recrystallisation from methanol

Sources & evidence

ORD record
ord-07ca96ad95334a79bd7a644b7595fcb8
Source dataset
uspto-grants-1988_09
Patent number
US04771058

Reaction notes

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