Methanesulfonic Acid → HCID 12017157, compound

HRID 2304872Notes

Reaction equation

HRID 2304872 reaction equation
CS(O)(=O)=O.[CH2:6]([O:8][C:9]([C:11]1[C:12](=[O:37])[C:13]2[C:28]([CH2:29][Br:30])=[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[S:26][C:14]=2[N:15]([CH2:17][C:18]2[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=2[F:25])[CH:16]=1)=[O:10])[CH3:7].[N+:38]([O-])([O-:40])=[O:39].[Na+]>>[CH2:6]([O:8][C:9]([C:11]1[C:12](=[O:37])[C:13]2[C:28]([CH2:29][Br:30])=[C:27]([C:31]3[CH:36]=[CH:35][C:34]([N+:38]([O-:40])=[O:39])=[CH:33][CH:32]=3)[S:26][C:14]=2[N:15]([CH2:17][C:18]2[C:19]([F:25])=[CH:20][CH:21]=[CH:22][C:23]=2[F:24])[CH:16]=1)=[O:10])[CH3:7]

Participants

4

Reactant 3

HCID 6395Methanesulfonic Acid2×HCID 24268Sodium NitrateHCID 12017156HCID 12017156, compound

Product 1

HCID 12017157HCID 12017157, compoundYield 75%

Procedure

To methanesulfonic acid (4.5 L), 900 g of the compound obtained in Example 1 described above was added over a period of 30 minutes (internal temperature 19 to 23° C.). After cooling on ice with stirring, sodium nitrate (147 g)/methanesulfonic acid (1.98 L) was added dropwise over a period of 2 hours (internal temperature 12 to 14° C.). Subsequently, the reaction mixture was stirred for 1.5 hours at 11 to 12° C., and was added to 155 L of an ice-water, and the precipitated crystal was recovered by a filtration, washed with water and then dried. 1The crystal was dried in vacuo for 26 hours at 50° C. to obtain 944 g of a crude product of the title compound (yield: 75%, HPLC). The crystal was suspended in ethyl acetate (2.9 L), and the mixture was stirred under reflux for 30 minutes, at room temperature for 30 minutes, and then stirred with cooling on ice for 1 hour and 20 minutes. The crystal was recovered by a filtration, washed with cool ethyl acetate (0.8 L), dried under reduced pressure for 8 hours at 50° C. to obtain 837 g of the title compound (yield: 86%).

Workup

  1. additionabove was added over a period of 30 minutes (internal temperature 19 to 23° C.)
  2. temperatureAfter cooling on ice
  3. stirringSubsequently, the reaction mixture was stirred for 1.5 hours at 11 to 12° C.
  4. filtrationthe precipitated crystal was recovered by a filtration
  5. washwashed with water
  6. customdried
  7. custom1The crystal was dried in vacuo for 26 hours at 50° C.

Sources & evidence

ORD record
ord-f8db96cd41384b20aab336fac8a8044f
Source dataset
uspto-grants-2002_08
Patent number
US06437132B2

Reaction notes

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