Toluene → HCID 86604720, compound

HRID 1367742Notes

Reaction equation

HRID 1367742 reaction equation
C1(C)C=CC=CC=1.[S:8](Cl)(=[O:11])(=[O:10])[NH2:9].CC(N(C)C)=O.[OH:19][CH2:20][CH2:21][O:22][CH:23]1[C:39]2([CH3:40])[CH:26]([CH:27]3[CH:36]([CH2:37][CH2:38]2)[C:35]2[CH:34]=[C:33]([O:41][CH3:42])[C:32]([OH:43])=[CH:31][C:30]=2[CH2:29][CH2:28]3)[CH2:25][CH2:24]1>C(OCC)(=O)C.C(Cl)(Cl)Cl.CO.O>[CH3:42][O:41][C:33]1[C:32]([O:43][S:8](=[O:11])(=[O:10])[NH2:9])=[CH:31][C:30]2[CH2:29][CH2:28][CH:27]3[CH:36]([CH2:37][CH2:38][C:39]4([CH3:40])[CH:26]3[CH2:25][CH2:24][CH:23]4[O:22][CH2:21][CH2:20][O:19][S:8](=[O:11])(=[O:10])[NH2:9])[C:35]=2[CH:34]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 31374DimethylacetamideHCID 66959677HCID 66959677, compound

Product 1

HCID 86604720HCID 86604720, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A toluene solution of sulfamoyl chloride (1 ml, 0.69 mmol) was evaporated to dryness, cooled to 0° C. and then treated with dimethylacetamide (1.5 mL) then diol 48 (45 mg). After 3 h stirring at rt the reaction was diluted in ethyl acetate (20 mL), then treated with water (10 ml), the organic layer was separated and extracted with brine (5×10 mL), dried and evaporated to give a yellow oil. Column chromatography (gradient 5-10% methanol in chloroform) was used to purify the desired bis-sulfamate 49 as a clear colourless oil (21 mg) which showed δH (CDCl3, TMS=0) 7.03 (1H, s, ArH), 6.90 (1H, s, ArH), 5.02 (4H, br, 2×NH2), 4.37-4.42 (2H, m, CH2OS), 3.87 (3H, s, OMe), 3.75-3.82 (2H, m, OCH2), 3.48 (1H, dd, J 8.6 & 7.9, OCH), 2.74-2.85 (2H, m, 6-CH2), 1.25-2.50 (H, m) and 0.79 (3H, s, 18-CH3); m/z 504.6.

Workup

  1. customthe organic layer was separated
  2. extractionextracted with brine (5×10 mL)
  3. customdried
  4. customevaporated
  5. customto give a yellow oil
  6. customto purify the desired bis-sulfamate 49 as a clear colourless oil (21 mg) which

Sources & evidence

ORD record
ord-864b5ce5c47342ad82b00dca48439f79
Source dataset
uspto-grants-2011_02
Patent number
US07893284B2

Reaction notes

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