HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Toluene → Sulfamic Acid 4-{3-[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-propylsulfanyl}-phenyl Ester

HRID 19904
Notes
Print preview

Reaction equation

HRID 19904 reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][CH2:21][CH2:22][CH2:23][N:24]([N:33]2[CH:37]=[N:36][N:35]=[CH:34]2)[C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)=[CH:16][CH:15]=1>O.C(OCC)(=O)C.CN(C)C(=O)C>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([N:24]([N:33]2[CH:37]=[N:36][N:35]=[CH:34]2)[CH2:23][CH2:22][CH2:21][S:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][S:1](=[O:4])(=[O:3])[NH2:2])=[CH:15][CH:16]=2)=[CH:26][CH:27]=1)#[N:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 219768664-{[3-(4-Hydroxy-phenylsulfanyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

Product 1

HCID 21044501Sulfamic Acid 4-{3-[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-propylsulfanyl}-phenyl Ester

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×
HCID 8857Ethyl AcetateSolvent
HCID 31374DimethylacetamideSolvent

Procedure

Sulphamoyl chloride solution in toluene (3 mL, 0.7 M, 2.1 mmol) was concentrated under reduced pressure (30° C. water bath temperature) to ca. 0.5 mL volume. The residue was cooled to 0° C. (ice bath) and N,N-dimethylacetamide (5 mL) was added. 4-{[3-(4-hydroxy-phenylsulfanyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile (CAB02182, 140 mg, 0.40 mmol) was added to the colourless solution and the mixture was stirred for 18 hours at room temperature. Ethyl acetate (50 mL) and water (50 mL) were added to the solution, the organic layer was separated, washed with water (2×30 mL) and brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in a small amount of acetone and precipitated by addition of hexane. The precipitate was filtered off and dried under high vacuum. Yield: 139 mg (81%) light yellow powder. 1H-NMR (400 MHz, d6-DMSO)=1.74 (tt, J=7.0, 7.0 Hz, 2H), 3.97 (t, J=7.0 Hz, 2H), 6.62 (d, J=9.0 Hz, 2H), 7.22 (d, J=8.6 Hz, 2H), 7.43 (d, J=8.6 Hz, 2H), 7.74 (d, J=9.0 Hz, 2H), 8.03 (s, 2H, —NH2), 9.00 (s, 2H). LRMS (FAB+): 431.1 (100, [M+H]+).

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water (2×30 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in a small amount of acetone
  7. customprecipitated by addition of hexane
  8. filtrationThe precipitate was filtered off
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-67810bad8e98498cb4e734d8a29833e6
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745472B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes