Acetic Acid → HCID 178512634, compound

HRID 261434Notes

Reaction equation

HRID 261434 reaction equation
[NH2:1][C:2]([NH:4][C:5]([NH2:7])=[NH:6])=[NH:3].Br[CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].C(O)(=O)C>CN(C)C=O>[NH:4]([C:5]1[NH:7][CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]2[C:16](=[O:25])[C:17]3=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]3[C:19]2=[O:20])[N:6]=1)[C:2]([NH2:1])=[NH:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14506404Bromomethyl 4-phthalimidobutyl ketoneHCID 176517607Carbamimidamidomethanimidamide

Product 1

HCID 178512634HCID 178512634, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Biguanide (1.01 g.) was stirred in dry dimethylformamide (15 ml.) and N-(6-bromo-5-oxohexyl)phthalimide (1.5 g.) added. The mixture was stirred for 3 hours, acetic acid (5 ml.) was then added and the total reaction mixture evaporated to dryness. The residue was dissolved in water (10 ml.) and extracted with ethyl acetate (5×20 ml.). The combined ethyl acetate extracts were evaporated to give a brown foam which was purified by column chromatography on silica gel using chloroform/methanol/ammonia (s.g. 0.880) 80:20:0.5 v/v/v. The appropriate fractions were evaporated to give 2-guanidino-4-(4-phthalimidobutyl)imidazole as a brown foam (0.3 g.).

Workup

  1. customthe total reaction mixture
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in water (10 ml.)
  4. extractionextracted with ethyl acetate (5×20 ml.)
  5. customThe combined ethyl acetate extracts were evaporated
  6. customto give a brown foam which
  7. customwas purified by column chromatography on silica gel
  8. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-b4a0b8520cf640b3ba9b9515c6d5bb0c
Source dataset
uspto-grants-1979_08
Patent number
US04165377

Reaction notes

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