Acetic Acid → N-(5,5,7,7-Tetramethyl-4,5,6,7-tetrahydrobenzothiazol-2-YL)urea

HRID 1577757Notes

Reaction equation

HRID 1577757 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.[O-:15][C:16]#[N:17].[K+].C(O)(=O)C>O>[CH3:13][C:8]1([CH3:14])[CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:16]([NH2:17])=[O:15])[S:3][C:4]=2[C:10]([CH3:12])([CH3:11])[CH2:9]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 127833484,5,6,7-tetrahydro-5,5,7,7-tetramethyl-2-Benzothiazolamine

Product 1

HCID 20569299N-(5,5,7,7-Tetramethyl-4,5,6,7-tetrahydrobenzothiazol-2-YL)urea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-5,5,7,7-tetramethyl-4,5,6,7-tetrahydrobenzothiazole (0.3mole), potassium cyanate (0.3 mole) and concentrated acetic acid (90 ml) are charged into a glass reaction vessel fitted with a mechanical stirrer and thermometer. A mild exotherm is noted at the beginning of the reaction. Stirring is continued for a period of about 1 hour with no external heating. Water (90 ml) is added and the resulting mixture filtered. The filtered-off solids are recrystallized from methanol to yield the desired product N-(5,5,7,7-tetramethyl-4-5,6,7-tetrahydrobenzothiazol-2-yl)urea.

Workup

  1. customfitted with a mechanical stirrer
  2. customA mild exotherm is noted at the beginning of the reaction
  3. filtrationthe resulting mixture filtered
  4. customThe filtered-off solids are recrystallized from methanol

Sources & evidence

ORD record
ord-102e186004c344ccab2c4599bc9b8e3f
Source dataset
uspto-grants-1981_09
Patent number
US04289524

Reaction notes

Loading…