Dichloromethane → HCID 12810767, compound

HRID 1659531Notes

Reaction equation

HRID 1659531 reaction equation
[Cl:1][C:2]1[N:6]([CH2:7][C:8]([NH:10][CH3:11])=O)[N:5]=[N:4][N:3]=1.C(Cl)Cl.C(Cl)(Cl)=O.[N-:19]=[N+:20]=[N-:21].CN(C)C(=[NH2+])N(C)C>N1C=CC=CC=1>[CH3:11][N:10]1[C:8]([CH2:7][N:6]2[C:2]([Cl:1])=[N:3][N:4]=[N:5]2)=[N:21][N:20]=[N:19]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6371PhosgeneHCID 12810766HCID 12810766, compoundHCID 178484365HCID 178484365, compound

Product 1

HCID 12810767HCID 12810767, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 1.75 g. (10 mmole) of 5-chloro-N-methyl-1H-tetrazol-1-acetamide, prepared as described under A above, in 50 ml. of methylene chloride containing 0.8 g. of pyridine and maintained at a temperature of about 0° C. was added with stirring excess phosgene. After addition was complete, the reaction mixture was stirred for 10 minutes without further cooling. The clear solution obtained on reaction was evaporated to dryness at a temperature of about 30° C. under reduced pressure. The residue containing the reaction product was suspended in 50 ml. of dioxane, and 2.4 g. (15.2 mmole) of tetramethylguanidinium azide were added to the suspension. The mixture was heated for 2 hours at the reflux temperature and after stirring overnight at room temperature, the reaction mixture was concentrated to near dryness under reduced pressure. The concentrate was dissolved in 30 ml. of water forming a pale yellow solution from which the product crystallized as colorless needles. The product was filtered and 0.4 g. of the crystalline product melting at about 138° C. to about 140° C. were obtained. A second crop of 0.5 g. of the product melting at about 136° C. to about 139° C. was isolated from the filtrate.

Workup

  1. additionTo a suspension of 1.75 g
  2. additionAfter addition
  3. customThe clear solution obtained on reaction
  4. customwas evaporated to dryness at a temperature of about 30° C. under reduced pressure
  5. additionThe residue containing the reaction product
  6. temperatureThe mixture was heated for 2 hours at the reflux temperature
  7. stirringafter stirring overnight at room temperature
  8. concentrationthe reaction mixture was concentrated
  9. dissolutionThe concentrate was dissolved in 30 ml
  10. customof water forming a pale yellow solution from which the product crystallized as colorless needles
  11. filtrationThe product was filtered

Sources & evidence

ORD record
ord-579f13ebce2c4f0eb652d9dcbecff6b7
Source dataset
uspto-grants-1981_12
Patent number
US04304774

Reaction notes

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