Water → HCID 53866075, compound

HRID 987525Notes

Reaction equation

HRID 987525 reaction equation
[CH2:1]([N:8]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20])[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>O1CCCC1>[CH2:1]([N:8]([C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20])[CH2:9][CH2:10][O:11][S:30]([CH3:29])(=[O:32])=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 18008929HCID 18008929, compound

Product 1

HCID 53866075HCID 53866075, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[benzyl-(4-bromo-2-nitro-phenyl)-amino]-ethanol (19.52 g, Reference Example 9) and triethylamine (7.8 ml) in anhydrous tetrahydrofuran (95 ml), at 25° C., was treated dropwise with methanesulphonyl chloride (4.75 ml). After stirring for 4 hours at 25° C. a further portion of methanesulphonyl chloride (4.75 ml) was added and stirring was continued for a further 16 hours at 25° C. The reaction mixture was treated with water (100 ml), the organic phase was separated and the aqueous phase was extracted three times with ethyl acetate (150 ml). The combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution (50 ml), then three times with distilled water (50 ml), then dried over magnesium sulphate and then evaporated under reduced pressure (2.7 kPa) at 40° C. to give the title compound (25.41 g) as a brown oil. 1H NMR, 300 MHz, (CD3)2SO: δ3.1 (s, 3H); 3.4 (t, 2H); 4.2 (t, 2H); 4.4 (s, 2H); 7.2(m, 5H); 7.4 (d, J=8 Hz, 1H); 7.7 (dd, J=8 Hz and J=1.5 Hz, 1H); 8 (d, J=1.5 Hz, 1H). MS (EI): M+ 430 and 428 (5%), 321 and 319 (20%), 91 (100%).

Workup

  1. additionwas added
  2. customthe organic phase was separated
  3. extractionthe aqueous phase was extracted three times with ethyl acetate (150 ml)
  4. washThe combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution (50 ml)
  5. dry with materialthree times with distilled water (50 ml), then dried over magnesium sulphate
  6. customevaporated under reduced pressure (2.7 kPa) at 40° C.

Sources & evidence

ORD record
ord-20f2658f71b1462f8c6b101b2fa38721
Source dataset
uspto-grants-2003_10
Patent number
US06632814B1

Reaction notes

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