Methyl Isocyanate → HCID 20367570, compound

HRID 616505Notes

Reaction equation

HRID 616505 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[C:3]=1[C:12]#[N:13].[CH3:14][N:15]=[C:16]=[O:17]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.O1CCCC1>[CH3:14][NH:15][C:16]([NH:1][C:2]1[S:6][N:5]=[C:4]([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[C:3]=1[C:12]#[N:13])=[O:17]

Participants

5

Reactant 2

HCID 12228Methyl Isocyanate2×HCID 20367579HCID 20367579, compound

Product 1

HCID 20367570HCID 20367570, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 16.0 g of 5-amino-4-cyano-3-(1-pyrrolidinyl)isothiazole, 25 drops of dibutyltin diacetate and 5.4 g of methyl isocyanate in 90 ml of tetrahydrofuran was heated under reflux for about 56 hours. Small increments of methyl isocyanate (3 ml at 27 hours and 2 ml at 40 hours) and dibutyltin diacetate (10 drops at 32 hours and 5 drops at 40 hours) were added during the reflux period. A solid that had formed was isolated by filtration. The filtrate was concentrated under reduced pressure to obtain a second crop. A total of 17.0 g of 1-methyl-3-(4-cyano-3-(1-pyrrolidinyl)-5-isothiazolyl)urea, m.p. 239°, was obtained. The nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for about 56 hours
  3. customA solid that had formed
  4. customwas isolated by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto obtain a second crop

Sources & evidence

ORD record
ord-5b8ccbbb7e504306b93ac8447ae854c0
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

Loading…