Methyl Isocyanate → HCID 54060546, compound

HRID 616518Notes

Reaction equation

HRID 616518 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([N:7]([CH2:9][CH2:10][CH2:11][CH3:12])[CH3:8])[C:3]=1[C:13]#[N:14].[CH3:15][N:16]=[C:17]=[O:18].C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC>O1CCCC1>[CH3:15][NH:16][C:17]([NH:1][C:2]1[S:6][N:5]=[C:4]([N:7]([CH2:9][CH2:10][CH2:11][CH3:12])[CH3:8])[C:3]=1[C:13]#[N:14])=[O:18]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 9798523Di-n-butyl diacetoxy tinHCID 53990496HCID 53990496, compound

Product 1

HCID 54060546HCID 54060546, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the manner of Example XI, part D, 7 g of 5-amino-3-(butylmethylamino)-4-cyanoisothiazole, 4.1 ml (4 g) of methyl isocyanate, and a catalytic amount of dibutyltin diacetate in 50 ml of tetrahydrofuran were allowed to react. The volatile materials were removed under reduced pressure and the residue was crystallized from 35 ml of 70:30 diethyl ether:hexane to yield solid material, mp 102° (decomposes). This material was recrystallized from 70 ml of 40:60 diethylether:hexane to yield 4.1 g of 1-methyl-3-(3-(butylmethylamino)-4-cyano-5-isothiazolyl)urea mp 169°-170°. The nmr spectrum was consistent with the assigned structure.

Workup

  1. customto react
  2. customThe volatile materials were removed under reduced pressure
  3. customthe residue was crystallized from 35 ml of 70:30 diethyl ether
  4. customhexane to yield solid material, mp 102° (decomposes)
  5. customThis material was recrystallized from 70 ml of 40:60 diethylether

Sources & evidence

ORD record
ord-5c593aae3ebb41cbbd39a74592f507b6
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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