Acetone → HCID 12223714, compound

HRID 1658060Notes

Reaction equation

HRID 1658060 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7]4=[C:8]([C:17](=[O:21])[NH:18][C:19](=[S:20])[N:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3.[OH-].[K+].[CH3:26]C(C)=O.CI>O>[CH3:26][S:20][C:19]1[N:6]2[C:7]3[C:12]([S:13][C:14]4[CH:15]=[CH:16][C:3]([C:2]([F:1])([F:22])[F:23])=[CH:4][C:5]=42)=[CH:11][CH:10]=[CH:9][C:8]=3[C:17](=[O:21])[N:18]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 12223713HCID 12223713, compound

Product 1

HCID 12223714HCID 12223714, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

10-Trifluoromethyl-1H-pyrimido[5,4,3-kl]phenothiazine-3-one-1(2H)-thione (53.6 g., 0.152 mol.) was added to a stirred solution of 8.95 g. (0.160 mol.) of potassium hydroxide in 1680 ml. of acetone and 720 ml. of water. After all the solid had dissolved and a clear yellow solution formed, 22.8 g. (10 ml., 0.160 mol.) of methyl iodide was added in one portion. The reaction mixture was stirred at 25° for 18 hours, diluted with 1000 ml. of water and chilled in an ice-bath for several hours. The resulting light yellow solid was collected by filtration and washed with water to give 1-methylmercapto-10-trifluoromethyl-3H-pyrimido[5,4,3-kl]phenothiazine-3-one, m.p. 229°-231° (ethanol).

Workup

  1. dissolutionAfter all the solid had dissolved
  2. customa clear yellow solution formed
  3. additiondiluted with 1000 ml
  4. filtrationThe resulting light yellow solid was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-4e2b4c933d614fffae55a6cf8bf5b2ad
Source dataset
uspto-grants-1976_06
Patent number
US03962438

Reaction notes

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