N,N'-Dimethylthiourea → HCID 20638581, compound

HRID 1275111Notes

Reaction equation

HRID 1275111 reaction equation
Cl.[CH3:2][N:3]1[C:7]2([OH:21])[C:8]3[CH:9]=[CH:10][C:11]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)=[CH:12][C:13]=3[CH2:14][CH:6]2[S:5][C:4]1=[N:22][CH3:23].[Cl:24]C1CC2C(=CC=C(C3C=NC=CC=3)C=2)C1=O.CNC(NC)=S>CO>[ClH:24].[CH3:2][N:3]1[C:7]2([OH:21])[C:8]3[CH:9]=[CH:10][C:11]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)=[CH:12][C:13]=3[CH2:14][CH:6]2[S:5][C:4]1=[N:22][CH3:23].[CH3:2][N:3]1[C:7]2([OH:21])[C:8]3[CH:9]=[CH:10][C:11]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)=[CH:12][C:13]=3[CH2:14][CH:6]2[S:5][C:4]1=[N:22][CH3:23]

Participants

6

Reactant 3

HCID 2723631N,N'-DimethylthioureaHCID 18407243HCID 18407243, compoundHCID 20638581HCID 20638581, compound

Product 2

HCID 20638581HCID 20638581, compoundHCID 20638582HCID 20638582, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Methyl-2-methylimino-6-pyridin-3-yl-2,3,8,8a-tetrahydroindeno-[1,2-d]thiazol-3a-ol hydrochloride: 366 mg of 2-chloro-5-pyridin-3-ylindan-1-one and 235 mg of N,N'-dimethylthiourea are dissolved in 5 ml of methanol and refluxed for 7 hours. The reaction mixture is cooled and concentrated in vacuo. The residue is treated with 5 ml of acetone, stirred in an ultrasonic bath for 30 minutes and then filtered off with suction. The residue is washed with acetone and dried in vacuo. The hydrochloride of 3-methyl-2-methylimino-6-pyridin-3-yl-2,3,8,8a-tetrahydroindeno-[1,2-d]thiazol-3a-ol having a melting point of 253-255° C. is obtained.

Workup

  1. temperaturerefluxed for 7 hours
  2. temperatureThe reaction mixture is cooled
  3. concentrationconcentrated in vacuo
  4. additionThe residue is treated with 5 ml of acetone
  5. filtrationfiltered off with suction
  6. washThe residue is washed with acetone
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7a93637e2902498397f88321d4e0fc2b
Source dataset
uspto-grants-2000_12
Patent number
US06159996

Reaction notes

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