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

HRID 1577754Notes

Reaction equation

HRID 1577754 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([CH3:12])([CH3:11])[CH2:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:5]=2[N:6]=1.[CH3:15][N:16]=[C:17]=[O:18].[N-]=C=O>C(OCC)(=O)C>[CH3:13][C:8]1([CH3:14])[CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:17]([NH:16][CH3:15])=[O:18])[S:3][C:4]=2[C:10]([CH3:12])([CH3:11])[CH2:9]1

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 105034IsocyanateHCID 127833484,5,6,7-tetrahydro-5,5,7,7-tetramethyl-2-Benzothiazolamine

Product 1

HCID 12783349N-(5,5,7,7-Tetramethyl-4,5,6,7-tetrahydrobenzothiazol-2-YL)-N'-methylurea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5,5,7,7-tetramethyl-4,5,6,7-tetrahydrobenzothiazole (21 grams; 0.1 mole) was dissolved in ethyl acetate (100 ml) and the solution charged into a glass reaction vessel fitted with a mechanical stirrer and themometer. Methyl isocyanate (6.2 grams 0.11 mole) was added dropwise to this solution over a period of 30 minutes. The temperature of the reactants was at about 20°-25° C. during the addition. At the conclusion of the isocyanate addition, stirring was continued at room temperature for a period of about 2 hours. The desired product, 2-amino-5,5,7,7-tetramethyl-4,5,6,7-tetrahydrobenzothiazole, a solid, was then filtered from the reaction mixture and air dried. Its melting point was greater than 250° C.

Workup

  1. additionthe solution charged into a glass reaction vessel
  2. customfitted with a mechanical stirrer
  3. additionThe temperature of the reactants was at about 20°-25° C. during the addition
  4. filtrationThe desired product, 2-amino-5,5,7,7-tetramethyl-4,5,6,7-tetrahydrobenzothiazole, a solid, was then filtered from the reaction mixture and air
  5. customdried

Sources & evidence

ORD record
ord-19c871d1ec5f49a3b2e5bf323111be6b
Source dataset
uspto-grants-1981_09
Patent number
US04289524

Reaction notes

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