Ammonia → 3-Methoxy-4-(4-phthalimidomethylbenzyloxy)benzamidine

HRID 745262Notes

Reaction equation

HRID 745262 reaction equation
C(Cl)(Cl)Cl.Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:31](=[O:32])[C:30]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]3[C:28]2=[O:37])=[CH:22][CH:21]=1)[C:11](=[NH:14])OC.[NH3:38]>CO>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[C:28](=[O:37])[C:29]3=[CH:36][CH:35]=[CH:34][CH:33]=[C:30]3[C:31]2=[O:32])=[CH:22][CH:21]=1)[C:11]([NH2:14])=[NH:38]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6212ChloroformHCID 23315107HCID 23315107, compound

Product 1

HCID 136552703-Methoxy-4-(4-phthalimidomethylbenzyloxy)benzamidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of 100 ml of chloroform and 100 ml of anhydrous methanol, was added 3.0 g of methyl 3-methoxy-4-(4-phthalimidomethylbenzyloxy)benzimidate hydrochloride followed by 16 ml of a methanol solution of anhydrous ammonia (22 mg/ml). The mixture was stirred for 24 hours and then evaporated to dryness. The residue was dissolved in methanol, then poured into a large volume of chloroform, and filtered from precipitated colorless solids. The filtrate was evaporated to dryness and the residue was recrystallized from methanol to yield 1.4 g of 3-methoxy-4-(4-phthalimidomethylbenzyloxy)benzamidine; m.p. 228°-230° C. To obtain a methanesulfonate, the above benzamidine compound was suspended in methanol and admixed with an excess of methanesulfonic acid. Upon addition of ether to the resulting solution, there was obtained a colorless solid which was recrystallized from methanol to yield colorless needle crystals of 3-methoxy-4-(4-phthalimidomethylbenzyloxy)benzamidine methanesulfonate; m.p. 174°-176° C.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in methanol
  3. additionpoured into a large volume of chloroform
  4. filtrationfiltered
  5. customfrom precipitated colorless solids
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-bd1758f223084b90a1e9550a1c91efeb
Source dataset
uspto-grants-1986_07
Patent number
US04598077

Reaction notes

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