Methanethiol → HCID 14402877, compound

HRID 1381823Notes

Reaction equation

HRID 1381823 reaction equation
[CH3:1][SH:2].Cl[CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:18].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:1][S:2][CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:18]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 11430Potassium CarbonateHCID 14402876HCID 14402876, compound

Product 1

HCID 14402877HCID 14402877, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Methyl mercaptan (1.9 g) is slowly introduced to a refluxing mixture composed of 4-chloromethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one (4.48 g), potassium carbonate (3.3 g) and methyl ethyl ketone (30 ml). The reaction mixture is refluxed for 5 hours, made free from methyl ethyl ketone by evaporation in vacuo, and the resultant residue is extracted with ethyl acetate. The extract is washed with saturated sodium carbonate aqueous solution and with water, dried over sodium sulfate, and condensed to ensure crystallization. The collected solid is washed with a small amount of ether to obtain 4-methylthiomethyl-6-nitro-2H-1,4-benzoxazin-3(4H)-one (2.3 g).

Workup

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. custommade free from methyl ethyl ketone by evaporation in vacuo
  3. extractionthe resultant residue is extracted with ethyl acetate
  4. washThe extract is washed with saturated sodium carbonate aqueous solution and with water
  5. dry with materialdried over sodium sulfate, and condensed
  6. customcrystallization
  7. washThe collected solid is washed with a small amount of ether

Sources & evidence

ORD record
ord-72f9e6c8d8d84a35a21dc6a570fe414f
Source dataset
uspto-grants-1989_02
Patent number
US04804394

Reaction notes

Loading…