Dimethyl Sulfate → HCID 13091588, compound

HRID 443901Notes

Reaction equation

HRID 443901 reaction equation
[CH3:1][C:2]1[C:13]([NH:14][CH:15]=[O:16])=[CH:12][C:5]2[N:6]3[CH2:11][CH2:10][N:9]=[C:7]3[S:8][C:4]=2[CH:3]=1.[CH3:17]N(C)P(=O)(N(C)C)N(C)C.[H-].[Na+].S(OC)(OC)(=O)=O>O.CC(C)CC(=O)C>[CH3:1][C:2]1[C:13]([N:14]([CH3:17])[CH:15]=[O:16])=[CH:12][C:5]2[N:6]3[CH2:11][CH2:10][N:9]=[C:7]3[S:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 12873986HCID 12873986, compound

Product 1

HCID 13091588HCID 13091588, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a stirred mixture of 5.5 parts of N-(2,3-dihydro-7-methylimidazo[2,1-b]benzothiazol-6-yl)formamide and 80 parts of hexamethylphosphoric triamide are added portionwise 1.24 parts of sodium hydride dispersion 75.8%. After stirring for 2 hours at room temperature, there are added dropwise 4.9 parts of dimethyl sulfate. Upon completion, stirring is continued for 3 hours at 50° C. and overnight at room temperature. 4-Methyl-2-pentanone and water are added and the layers are separated. The aqueous phase is extracted twice with 4-methyl-2-pentanone. The combined organic phases are washed with water, dried, filtered and evaporated. The residue is crystallized from methylbenzene. The product is filtered off and dried, yielding 1.5 parts of N-(2,3-dihydro-7-methylimidazo[2,1-b]benzothiazol-6-yl)-N-methylformamide; mp. 164.2° C.

Workup

  1. stirringUpon completion, stirring
  2. waitis continued for 3 hours at 50° C. and overnight at room temperature
  3. customthe layers are separated
  4. extractionThe aqueous phase is extracted twice with 4-methyl-2-pentanone
  5. washThe combined organic phases are washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from methylbenzene
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-3a2528be323f42cf8dc5ed196b2d1b02
Source dataset
uspto-grants-1981_04
Patent number
US04262004

Reaction notes

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