N,N'-Dimethylthiourea → 5-Methanesulfonyl-3-methyl-2-methylimino-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol

HRID 1595239Notes

Reaction equation

HRID 1595239 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:8]=2)[C:3]1=[O:15].[CH3:16][NH:17][C:18]([NH:20][CH3:21])=[S:19]>CC(C)=O>[CH3:14][S:11]([C:6]1[CH:7]=[CH:8][C:9]2[CH2:10][CH:2]3[S:19][C:18](=[N:17][CH3:16])[N:20]([CH3:21])[C:3]3([OH:15])[C:4]=2[CH:5]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 2723631N,N'-DimethylthioureaHCID 184072332-Bromo-6-methanesulfonyl-1-indanone

Product 1

HCID 217049405-Methanesulfonyl-3-methyl-2-methylimino-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

1.45 g of 2-bromo-6-methanesulfonyl-1-indanone are dissolved in 15 ml of acetone and, while stirring, 0.65 g of N,N′-dimethylthiourea in 10 ml of acetone is added. The solution is initially clear but, after about 10 min, the hydrobromide of 5-methanesulfonyl-3-methyl-2-methylimino-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol crystallizes out. Stirring at room temperature for 1 h is followed by filtration with suction and washing with a little acetone. 2.1 g of hydrobromide (melting point 265° C.) are suspended in 10 ml of methanol, and 1 ml of triethylamine is added. After 15 min, 150 ml of water is added, and the mixture is stirred while cooling in ice for 1 h. The product which is formed is filtered off with suction and washed with a little cold water. 5-Methanesulfonyl-3-methyl-2-methylimino-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol is obtained with a melting point of 158° C.

Workup

  1. customthe hydrobromide of 5-methanesulfonyl-3-methyl-2-methylimino-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol crystallizes out
  2. stirringStirring at room temperature for 1 h
  3. filtrationis followed by filtration with suction
  4. washwashing with a little acetone
  5. addition1 ml of triethylamine is added
  6. waitAfter 15 min
  7. addition150 ml of water is added
  8. stirringthe mixture is stirred
  9. temperaturewhile cooling in ice for 1 h
  10. customThe product which is formed
  11. filtrationis filtered off with suction
  12. washwashed with a little cold water

Sources & evidence

ORD record
ord-c9c0c59d47ed4912aad6cb648c463f73
Source dataset
uspto-grants-2001_09
Patent number
US06288093B1

Reaction notes

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