Dimethylcarbamoyl Chloride → HCID 21524640, compound

HRID 917971Notes

Reaction equation

HRID 917971 reaction equation
[CH3:1][N:2]1[C:6]([C:7]#[N:8])=[C:5]([N+:9]([O-:11])=[O:10])[N:4]=[C:3]1[CH2:12][OH:13].[CH3:14][N:15]([CH3:19])[C:16](Cl)=[O:17]>N1C=CC=CC=1>[CH3:1][N:2]1[C:6]([C:7]#[N:8])=[C:5]([N+:9]([O-:11])=[O:10])[N:4]=[C:3]1[CH2:12][O:13][C:16](=[O:17])[N:15]([CH3:19])[CH3:14]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 14638340HCID 14638340, compound

Product 1

HCID 21524640HCID 21524640, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.8 G. (0.01 moles) of 1-methyl-2-hydroxymethyl-4-nitro-5-cyanoimidazole and 2.14 g. (0.12 moles) of dimethylcarbamoyl chloride are combined in 15 ml. of pyridine and heated at 100°C. for 24 hours. The reaction mixture is evaporated to dryness, treated with 50 ml. of water and extracted with methylene chloride. The combined methylene chloride extracts are washed with water, dried, evaporated to dryness and the residue triturated with ether. The solid material is filtered and crystallized from isopropanol affording 1-methyl-2-(N,N-dimethylcarbamoyloxymethyl)-4-nitro-5-cyanoimidazole, m.p. 85° to 88°C.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. additiontreated with 50 ml
  3. extractionof water and extracted with methylene chloride
  4. washThe combined methylene chloride extracts are washed with water
  5. customdried
  6. customevaporated to dryness
  7. customthe residue triturated with ether
  8. filtrationThe solid material is filtered
  9. customcrystallized from isopropanol

Sources & evidence

ORD record
ord-5e057333186342ce8642cf44e5363a19
Source dataset
uspto-grants-1976_07
Patent number
US03968228

Reaction notes

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