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Triphenylphosphine → 1-(2-Morpholin-2-ylethyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1818820
Notes
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Reaction equation

HRID 1818820 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[NH:9][S:8]2(=[O:17])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:38][CH2:39][CH:40]1[O:45][CH2:44][CH2:43][N:42](C(OC(C)(C)C)=O)[CH2:41]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[NH:42]1[CH2:43][CH2:44][O:45][CH:40]([CH2:39][CH2:38][N:9]2[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8]2(=[O:16])=[O:17])[CH2:41]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 44182317tert-Butyl 2-(2-hydroxyethyl)morpholine-4-carboxylateHCID 468330931-Phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

Product 1

HCID 547569241-(2-Morpholin-2-ylethyl)-3-phenyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxideYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-phenyl-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.2 g, 0.8 mmol) in THF (10 mL) was added triphenylphosphine (0.26 g, 1 mmol), tert-butyl 2-(2-hydroxyethyl)morpholine-4-carboxylate (0.2 g, 0.9 mmol) and DIAD (0.2 g, 1 mmol) at 0° C. The mixture was allowed to warm to ambient temperature overnight then concentrated and chromatographed on silica gel (0 to 40% EtOAC in hexane). The resulting mostly pure carbamate was dissolved in dichloromethane (10 mL) and treated with HCL (4 mL, 4M in dioxane). The resulting salt was chromatographed on silica (0 to 100% of (7N NH3/MeOH) in dichloromethane) giving the desired product as a clear oil (0.23 g, 80%). HRMS: calcd for C18H21N3O3S+H+, 360.1376; found (ESI, [M+H]+), 360.1377.

Workup

  1. concentrationthen concentrated
  2. customchromatographed on silica gel (0 to 40% EtOAC in hexane)
  3. dissolutionThe resulting mostly pure carbamate was dissolved in dichloromethane (10 mL)
  4. additiontreated with HCL (4 mL, 4M in dioxane)
  5. customThe resulting salt was chromatographed on silica (0 to 100% of (7N NH3/MeOH) in dichloromethane)

Sources & evidence

ORD record
ord-925fb8f9c4614bedbce2345bbef1660d
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601722B2

Reaction notes

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