Ammonia → HCID 20184624, compound

HRID 2413132Notes

Reaction equation

HRID 2413132 reaction equation
[CH2:1]([N:4]=[C:5]([NH2:19])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18])[N:8]=1)[CH2:2][CH3:3].S(=O)(=O)(O)[OH:21].N>>[CH2:1]([N:4]=[C:5]([NH2:19])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH2:18])=[O:21])[N:8]=1)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 20137146HCID 20137146, compound

Product 1

HCID 20184624HCID 20184624, compound

Procedure

A mixture of 5-(4-[2-propylguanidino]pyrimid-2-yl)valeronitrile (0.25 g.) and concentrated sulphuric acid (2 ml.) was stirred at ambient temperature for 3.5 hours. The reaction mixture was cooled in an ice bath and basified by careful dropwise addition of concentrated aqueous ammonia (s.g. 0.880). The resulting white precipitate was collected, washed with water and allowed to dry. The solid was purified by medium pressure chromatography on silica gel using CHCl3 /MeOH/aqueous ammonia (s.g. 0.880) 8:2:0.3 v/v/v as eluant to give 5-(4-[2-propylguanidino]pyrimid-2-yl)valeramide (0.15 g.), m.p. 212°-214°.

Workup

  1. customThe resulting white precipitate was collected
  2. washwashed with water
  3. customto dry
  4. customThe solid was purified by medium pressure chromatography on silica gel

Sources & evidence

ORD record
ord-20f9d790db224060aad7da8d676b276a
Source dataset
uspto-grants-1985_01
Patent number
US04496564

Reaction notes

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