Dimethylformamide → 2-{2-[(Dimethylaminomethylene)amino]-5-thiadiazolyl}-1-methyl-5-nitroimidazole

HRID 462222Notes

Reaction equation

HRID 462222 reaction equation
[NH2:1][N:2]1[NH:6][CH:5]=[C:4]([C:7]2[N:8]([CH3:15])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=2)[S:3]1.C1C(=NNC2C=CC(/C=C/C3C=CC(NN=C4C=CC(=O)C=C4)=CC=3S([O-])(=O)=O)=C(S([O-])(=O)=O)C=2)C=CC(=O)C=1.[Na+].[Na+].[CH3:58][N:59]([CH3:62])[CH:60]=O>>[CH3:58][N:59]([CH:62]=[N:1][N:2]1[NH:6][CH:5]=[C:4]([C:7]2[N:8]([CH3:15])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=2)[S:3]1)[CH3:60]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 213908162-(2-Amino-5-thiadiazolyl)-1-methyl-5-nitroimidazoleHCID 178516258HCID 178516258, compound

Product 1

HCID 681200132-{2-[(Dimethylaminomethylene)amino]-5-thiadiazolyl}-1-methyl-5-nitroimidazole

Procedure

Phosgene gas is bubbled into 100 ml. of N,N-dimethylformamide at 5°-10° C. until 2.0 g. (0.02 mole) is absorbed and a crystalline suspension is formed. This suspension is added in portions to a stirred mixture of 4.5 g. (0.02 mole) of 2-(2-amino-5-thiadiazolyl)-1-methyl-5-nitroimidazole and 100 ml. of N,N-dimethylformamide at 25° C. After 30 minutes the reaction mixture is diluted with 200 ml. of diethyl ether, and the pale yellow solid is collected, washed with ether, and dried. Treatment of this material with 150 ml. of water and drying affords 5.0 g. (89%) of brilliant yellow solid melting at 230°-232° C.

Workup

  1. customPhosgene gas is bubbled into 100 ml
  2. customat 5°-10° C.
  3. custom(0.02 mole) is absorbed
  4. customa crystalline suspension is formed
  5. additionThis suspension is added in portions to a stirred mixture of 4.5 g
  6. customat 25° C
  7. additionAfter 30 minutes the reaction mixture is diluted with 200 ml
  8. customof diethyl ether, and the pale yellow solid is collected
  9. washwashed with ether
  10. customdried
  11. dry with materialof water and drying
  12. customaffords 5.0 g

Sources & evidence

ORD record
ord-3cf639959bec45ce9954e395ca06e15f
Source dataset
uspto-grants-1977_12
Patent number
US04065567

Reaction notes

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