Bromomethyl 4-phthalimidobutyl ketone → 2-(2-Methylguanidino)-4-(4-phthalimidobutyl)thiazole hydrobromide

HRID 261429Notes

Reaction equation

HRID 261429 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]([NH2:8])=[S:7])=[NH:4].[Br:9][CH2:10][C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26]>C(O)C>[BrH:9].[CH3:1][N:2]=[C:3]([NH2:4])[NH:5][C:6]1[S:7][CH:10]=[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]2[C:17](=[O:26])[C:18]3=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]3[C:20]2=[O:21])[N:8]=1

Participants

4

Reactant 2

HCID 14506404Bromomethyl 4-phthalimidobutyl ketoneHCID 178485127(N-methylamidino)thiourea

Product 1

HCID 202801622-(2-Methylguanidino)-4-(4-phthalimidobutyl)thiazole hydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (N-methylamidino)thiourea (0.4 g.) in hot ethanol (20 ml.) was added N-(6-bromo-5-oxohexyl)phthalimide (1.5 g.). The mixture was heated under reflux for 1 hour, cooled and evaporated to dryness. The residue was triturated with acetonitrile and the resulting solid was filtered and dried to give 2-(2-methylguanidino)-4-(4-phthalimidobutyl)thiazole hydrobromide, m.p. 210°-212° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. customevaporated to dryness
  5. customThe residue was triturated with acetonitrile
  6. filtrationthe resulting solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-2e89abdc7cdb422fa4c7a726a66b98d2
Source dataset
uspto-grants-1979_08
Patent number
US04165377

Reaction notes

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