Water → HCID 3692330, compound

HRID 1064337Notes

Reaction equation

HRID 1064337 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(N(CC)CC)C.O>C(Cl)Cl>[O:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][CH2:13][NH:12][S:8]([C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 73994-Iodobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 61055N-(3-Aminopropyl)morpholine

Product 1

HCID 3692330HCID 3692330, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Iodophenylsulphonyl chloride (3.03 g, 10 mmol) in DCM (30 ml) was added dropwise over 15 minutes to a solution of 4-(3-aminopropyl)morpholine (1.75 ml, 12 mmol) and triethylamine (1.7 ml, 12 mmol) in DCM (50 ml) cooled in an ice bath. The mixture was allowed to warm to ambient temperature and stirred for 15 minutes. Water (50 ml) was added and the phases separated. The organic layer was washed with water (50 ml) and brine (50 ml), dried (Chemelut column 1010) and evaporated to give the title compound (4.10 g, 100%) as a beige solid. NMR 1.70 (m, 2H), 2.43 (m, 6), 3.14 (t, 2H), 3.71 (m, 4H), 7.08 (s, 1H), 7.58 (d, 2H), 7.85 (d, 2H); m/z 411.

Workup

  1. temperaturecooled in an ice bath
  2. customthe phases separated
  3. washThe organic layer was washed with water (50 ml) and brine (50 ml)
  4. customdried (Chemelut column 1010)
  5. customevaporated

Sources & evidence

ORD record
ord-6a77465a409b43d688caddced61cd7f2
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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