Ammonia → HCID 21504501, compound

HRID 1288273Notes

Reaction equation

HRID 1288273 reaction equation
[CH3:1][O:2][C:3]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:4]=1[C:5](=[NH:9])OCC.[NH3:15].[ClH:16]>C(O)C.C(OCC)C>[ClH:16].[CH3:1][O:2][C:3]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:4]=1[C:5]([NH2:9])=[NH:15]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 21504428HCID 21504428, compound

Product 1

HCID 21504501HCID 21504501, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

Ethyl 2-methoxy-3-methylbenzimidate borofluoride (28 g.) was mixed with a saturated anhydrous solution of ammonia in ethanol (46 ml.), the mixture was kept at room temperature in a stoppered vessel for 3 days and then evaporated to dryness in vacuo. The residue was dissolved in water (25 ml.) and treated with 5N sodium hydroxide solution (50 ml.). The solution was saturated with sodium chloride and extracted with diethyl ether. The extract was dried over potassium hydroxide and evaporated to give crude 2-methoxy-3-methylbenzamidine, m.p. 72°-74° C. This was dissolved in anhydrous ethanol (40 ml.) and the solution treated with a saturated anhydrous solution of hydrogen chloride in diethyl ether (100 ml.), and diluted with anhydrous diethyl ether (100 ml.). The solid which separated was filtered off and washed with anhydrous diethyl ether to give 2-methoxy-3-methylbenzamidine hydrochloride (17.8 g.), m.p. 208°-209° C. (with decomposition).

Workup

  1. customevaporated to dryness in vacuo
  2. dissolutionThe residue was dissolved in water (25 ml.)
  3. additiontreated with 5N sodium hydroxide solution (50 ml.)
  4. extractionextracted with diethyl ether
  5. dry with materialThe extract was dried over potassium hydroxide
  6. customevaporated
  7. customto give crude 2-methoxy-3-methylbenzamidine, m.p. 72°-74° C
  8. customThe solid which separated
  9. filtrationwas filtered off
  10. washwashed with anhydrous diethyl ether

Sources & evidence

ORD record
ord-cd9a99b1730f4009b48728828ad88cf7
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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