Diphenylthiourea → 5-Methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol

HRID 1275109Notes

Reaction equation

HRID 1275109 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].[C:16]1([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[S:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(C)=O>[CH3:14][S:11]([C:6]1[CH:7]=[CH:8][C:9]2[CH2:10][CH:2]3[S:24][C:23](=[N:22][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:3]3([OH:15])[C:4]=2[CH:5]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 700999DiphenylthioureaHCID 184072332-Bromo-6-methanesulfonyl-1-indanone

Product 1

HCID 221190295-Methanesulfonyl-3-phenyl-2-phenylimino-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-methanesulfonylindan-1-one are dissolved in 15 ml of acetone and treated with stirring with 1.25 g of N,N'-diphenylthiourea in 25 ml of acetone. The hydrobromide of 5-methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8a-tetrahydro-indeno[1,2-d]thiazol-3a-ol crystallizes out of the clear solution after about 2 hours. After standing overnight, it is filtered off with suction and washed with a little acetone. 1.7 g of hydrobromide (m.p. 247° C.) are dissolved in 10 ml of methanol and treated with 0.8 ml of triethylamine. After 15 min, 150 ml of water are added and the mixture is stirred for 30 min with ice-cooling. The product formed is filtered off with suction and washed with a little cold water. 5-Methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol of melting point 172° C. is obtained.

Workup

  1. additiontreated
  2. customThe hydrobromide of 5-methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8a-tetrahydro-indeno[1,2-d]thiazol-3a-ol crystallizes out of the clear solution after about 2 hours
  3. filtrationit is filtered off with suction
  4. washwashed with a little acetone
  5. dissolution1.7 g of hydrobromide (m.p. 247° C.) are dissolved in 10 ml of methanol
  6. additiontreated with 0.8 ml of triethylamine
  7. waitAfter 15 min
  8. addition150 ml of water are added
  9. temperaturecooling
  10. customThe product formed
  11. filtrationis filtered off with suction
  12. washwashed with a little cold water

Sources & evidence

ORD record
ord-bdd15d627312450fa5234676af076805
Source dataset
uspto-grants-2000_12
Patent number
US06159996

Reaction notes

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