Ammonia → HCID 178514025, compound

HRID 895054Notes

Reaction equation

HRID 895054 reaction equation
[C:1]([CH2:4][N:5]1[C:9]([SH:10])=[N:8][N:7]=[N:6]1)(O)=[O:2].O1CCCC1.[NH3:16]>CCOCC>[C:1]([CH2:4][N:5]1[C:9]([SH:10])=[N:8][N:7]=[N:6]1)(=[O:2])[NH2:16]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 178525857HCID 178525857, compound

Product 1

HCID 178514025HCID 178514025, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Carboxymethyltetrazole-5-thiol and 1,1-carbonyldiimidazole were reacted as described in Example 4. To the reaction mixture was added tetrahydrofuran saturated with dry ammonia gas. The resulting suspension was stirred for 2.5 hours and the solid which formed was collected by filtration, washed with tetrahydrofuran and dissolved in methanol. Amberlite IR-120 ion-exchange resin (50 g.) was added and the suspension was stirred for 15 minutes. The resin was then removed and washed with absolute methanol. The methanol solution was concentrated to give a residue which was dissolved in ether and triturated with acetone to give 1-carbamoylmethyltetrazole-5-thiol, m.p. 200° (dec.).

Workup

  1. customthe solid which formed
  2. filtrationwas collected by filtration
  3. washwashed with tetrahydrofuran
  4. dissolutiondissolved in methanol
  5. additionAmberlite IR-120 ion-exchange resin (50 g.) was added
  6. stirringthe suspension was stirred for 15 minutes
  7. customThe resin was then removed
  8. washwashed with absolute methanol
  9. concentrationThe methanol solution was concentrated
  10. customto give a residue which
  11. customtriturated with acetone

Sources & evidence

ORD record
ord-6babe9034a6c494886c117150ab94a2d
Source dataset
uspto-grants-1981_08
Patent number
US04286089

Reaction notes

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