Acetic Acid → HCID 178502054, compound

HRID 255539Notes

Reaction equation

HRID 255539 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH2:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(O)(=[O:15])C.O.[C:18]([NH:22][C:23](=N)SC)([O:20][CH3:21])=[O:19]>C(O)C>[OH2:15].[NH:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[C:23]1[NH:22][C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 15142893,4-DiaminoquinolineHCID 145796808N-carbomethoxy-S-methylisothiourea

Product 1

HCID 178502054HCID 178502054, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 6.6 g (0.041 mole) of 3,4-diaminoquinoline (from Example 39), 2.0 ml of glacial acetic acid, 35 cc of ethanol and 35 ml of water was added 9.3 g (0.045 mole) of N-carbomethoxy-S-methylisothiourea, and the mixture was heated at its reflux temperature for two hours. Evaporation provided a residue which was suspended in ethanol, separated by filtration and washed with water. Recrystallization from ethanol provided methyl 1H-imidazo[4,5-c]quinolin-2-carbamate hydrate, m.p. >250° C. Analysis: Calculated for C12H10N4O2. 0.75H2O: %C, 56.4; %H, 4.5; %N, 21.9; Found: %C, 56.1; %H, 4.4; %N, 22.4.

Workup

  1. temperaturethe mixture was heated at its
  2. temperaturereflux temperature for two hours
  3. customEvaporation
  4. customprovided a residue which
  5. customseparated by filtration
  6. washwashed with water
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-0e2730d88efe48169e176305209b589a
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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