Water → HCID 13922870, compound

HRID 979568Notes

Reaction equation

HRID 979568 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:15][C:16]1[CH:28]=[CH:27][C:19]2[S:20][C:21]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:22][C:18]=2[CH:17]=1.O>CO>[N:1]1([CH2:15][C:16]2[CH:28]=[CH:27][C:19]3[S:20][C:21]([S:23](=[O:25])(=[O:26])[NH2:24])=[CH:22][C:18]=3[CH:17]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 13922868HCID 13922868, compound

Product 1

HCID 13922870HCID 13922870, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of morpholine (0.91 g, 10.5 mmol) and triethylamine (1.01 g, 10 mmol) in 20 ml of methanol was added 5-bromomethyl-2-sulfamoylbenzo[b]thiophene (3.06 9, 10 mmol) portionwise over 5 minutes at ambient temperature. Stirring was continued for 11/4 hours. The resulting suspension was cooled and filtered after an additional 1 hour to give 2.76 g. of yellow solid. Concentration of the filtrate in vacuo followed by trituration of the residue with water and filtering gave an additional 0.3 g of yellow solid. (Total crude yield was 98%). Recrystallization from nitromethane gave material with m.p. 221.5°-224° C.

Workup

  1. custom4 hours
  2. temperatureThe resulting suspension was cooled
  3. filtrationfiltered after an additional 1 hour
  4. customto give 2.76 g
  5. filtrationfiltering

Sources & evidence

ORD record
ord-4355a688628f4cb0904fd9285eb9fc92
Source dataset
uspto-grants-1987_05
Patent number
US04668697

Reaction notes

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