Dimethyl Sulfoxide → Diethyl 2-amino-6-{[(N-methylamino)-carbonyloxy-carbamoyl]-methyl}-azulene-1,3-dicarboxylate

HRID 1954351Notes

Reaction equation

HRID 1954351 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:17][C:18](=[O:21])[NH:19][OH:20])[CH:8]=[CH:9]2)[C:3]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].CS(C)=O.[CH3:31][N:32]=[C:33]=[O:34]>O>[NH2:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:17][C:18](=[O:21])[NH:19][O:20][C:33]([NH:32][CH3:31])=[O:34])[CH:8]=[CH:9]2)[C:3]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 12228Methyl IsocyanateHCID 9863689Diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate

Product 1

HCID 23296717Diethyl 2-amino-6-{[(N-methylamino)-carbonyloxy-carbamoyl]-methyl}-azulene-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.2 g (0.55 mmol) of diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate, 5 ml of dimethyl sulphoxide and 35 □l (0.6 mmol) of methyl isocyanate is stirred at room temperature for 18 hours. Thereafter, the mixture is diluted with water, extracted with dichloromethane and the extract is chromatographed on silica gel. Elution with ethyl acetate gives 60 mg (36% of theory) of the title compound of m.p. 222-224° C.

Workup

  1. extractionextracted with dichloromethane
  2. customthe extract is chromatographed on silica gel
  3. washElution with ethyl acetate

Sources & evidence

ORD record
ord-a28ba3edcafc41b9b29ee93afb7d5f3e
Source dataset
uspto-grants-2000_09
Patent number
US06121322

Reaction notes

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