Methyl Isocyanate → N-(5,5,7-trimethyl-4,5,6,7-tetrahydrobenzothiazol-2-yl)-N'-methylurea

HRID 1577758Notes

Reaction equation

HRID 1577758 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]([CH3:11])[CH2:9][C:8]([CH3:13])([CH3:12])[CH2:7][C:5]=2[N:6]=1.[CH3:14][N:15]=[C:16]=[O:17]>C(OCC)(=O)C>[CH3:13][C:8]1([CH3:12])[CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:16]([NH:15][CH3:14])=[O:17])[S:3][C:4]=2[CH:10]([CH3:11])[CH2:9]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 205484722-Amino-5,5,7-trimethyl-4,5,6,7-tetrahydrobenzothiazole

Product 1

HCID 20569296N-(5,5,7-trimethyl-4,5,6,7-tetrahydrobenzothiazol-2-yl)-N'-methylurea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5,5,7-trimethyl-4,5,6,7-tetrahydrobenzothiazole (0.1 mole) is dissolved in ethyl acetate (100 ml) and the solution is charged into a glass reaction vessel fitted with a stirrer and thermometer. Methyl isocyanate (0.11 mole) is added dropwise to this solution over a period of about 30 minutes. The temperature of the reactant is held at about 20° C. to 30° C. during the addition. At the end of the addition, stirring is continued at room temperature for a period of about 2 hours. The reaction mixture is then filtered and the filtered-off solids are air dried to yield the desired product N-(5,5,7-trimethyl-4,5,6,7-tetrahydrobenzothiazol-2-yl)-N'-methylurea.

Workup

  1. additionthe solution is charged into a glass reaction vessel
  2. customfitted with a stirrer
  3. additionThe temperature of the reactant is held at about 20° C. to 30° C. during the addition
  4. additionAt the end of the addition
  5. filtrationThe reaction mixture is then filtered
  6. customdried

Sources & evidence

ORD record
ord-7777590c1fce48ce85448ca03943b192
Source dataset
uspto-grants-1981_09
Patent number
US04289524

Reaction notes

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