Sodium Bicarbonate → HCID 10811332, compound

HRID 1654312Notes

Reaction equation

HRID 1654312 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[OH:8])[CH3:2].C(=O)(O)[O-].[Na+].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]([F:33])[F:32]>C(#N)C>[CH2:1]([N:3]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]([F:33])[F:32])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][CH:14]=1)[OH:8])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10655680HCID 10655680, compoundHCID 10779588N-(4-(4-(ethylamino)-1-hydroxybutyl)phenyl)methanesulfonamide

Product 1

HCID 10811332HCID 10811332, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Procedure B (Example 17, Step IV), a stirred mixture of N-[4-[4-(ethylamino)-1-hydroxybutyl]phenyl]methanesulfonamide (Example 7, Step II) and sodium bicarbonate in acetonitrile was allowed to react with 1-bromo-6,6-difluorohexane (Step II) to give N-[4-[4-[ethyl(6,6-difluorohexyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide, a compound of Formula I'. A mixture of this compound and 0.5 equivalents of fumaric acid was crystallized from acetone to give the titled product, mp 88°-90° C. Anal. calc'd for C21H34F2N2O5S: C, 54.29; H, 7.38; N, 6.03; S, 6.90. Found: C, 54.42; H, 7.58; N, 5.74; S, 6.58.

Sources & evidence

ORD record
ord-da4517defa4548e1b48456c7cdfdbed1
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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