Hydrochloric Acid → 4-[7-Propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butyl methanesulfonate

HRID 1245340Notes

Reaction equation

HRID 1245340 reaction equation
[CH2:1]([C:4]1[C:12]2[O:11][N:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[C:8]=2[CH:7]=[CH:6][C:5]=1[CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH2:2][CH3:3].CCN(CC)CC.[CH3:29][S:30](Cl)(=[O:32])=[O:31].Cl>C(Cl)Cl>[CH3:29][S:30]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][C:5]1[CH:6]=[CH:7][C:8]2[C:9]([C:13]([F:15])([F:14])[F:16])=[N:10][O:11][C:12]=2[C:4]=1[CH2:1][CH2:2][CH3:3])(=[O:32])=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 219110454-[7-Propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butan-1-ol

Product 1

HCID 219109934-[7-Propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[7-propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl]butan-1-ol, from this Example step 4, in CH2Cl2 (25 mL) was added Et3N (0.42 mL, 2.99 mmol) and methanesulfonyl chloride (0.17 mL, 2.2 mmol) at 0° C. The mixture was stirred from 0° C. to room temperature for 2 hours. 0.5N HCl was added and the mixture extracted 3 times with CH2Cl2. Combined organic extracts were washed with water and brine then dried over Na2SO4. The solvent was evaporated in vacuo to give the title compound.

Workup

  1. customat 0° C
  2. extractionthe mixture extracted 3 times with CH2Cl2
  3. washCombined organic extracts were washed with water and brine
  4. dry with materialthen dried over Na2SO4
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4cae43739b904ced8bdc1c09e6f3f22f
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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