Dimethyl Sulfate → 5-Chloro-3-methyl-6-nitrobenzo[d]oxazol-2(3H)-one

HRID 2401490Notes

Reaction equation

HRID 2401490 reaction equation
[Cl:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[CH3:15]OS(OC)(=O)=O>>[Cl:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH3:15])[C:6]=2[CH:11]=1

Participants

3

Reactant 2

HCID 6497Dimethyl SulfateHCID 2415982(3h)-benzoxazolone, 5-chloro-6-nitro-

Product 1

HCID 3374635-Chloro-3-methyl-6-nitrobenzo[d]oxazol-2(3H)-one

Procedure

5-Chloro-3-methyl-6-nitrobenzo[d]oxazol-2(3H)-one was prepared by the procedure described in Example 2, step 2 starting from 5-chloro-6-nitrobenzo[d]oxazol-2(3H)-one (1.75 g, 8.1 mmol) substituting iodomethane for dimethylsulfate. The crude product was recrystallised from methanol to afford an orange solid (0.6 g, 32%), which was taken through to the next step with no further purification.

Workup

  1. customThe crude product was recrystallised from methanol

Sources & evidence

ORD record
ord-f78f30c5cb274594bd2786d81a716d2a
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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