Hydrochloric Acid → HCID 22311005, compound

HRID 2305585Notes

Reaction equation

HRID 2305585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:15]([OH:17])=O.[C:22]1([S:28]([NH2:31])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN(C1C=CC=CN=1)C.Cl.C(N=C=NCCCN(C)C)C.Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:15]([NH:31][S:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:30])=[O:29])=[O:17]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15290299HCID 15290299, compound

Product 1

HCID 22311005HCID 22311005, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(3,4-dichlorobenzyl)indole-2-carboxylic acid (0.23 g), benzenesulphonamide (129 mg), dimethylaminopyridine (0.22 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.19 g) in dichloromethane was allowed to stir for 24 hours at room temperature. 2N HCl was added and the reaction stirred vigorously for 2 hours, then extracted with dichloromethane. Combined organic extracts were dried (MgSO4) and concentrated to yield the desired end product as a white crystalline solid (122 mg, 32%); NMR δ(CD3SOCD3) 5.65 (s, 2H), 6.73 (dd, 1H), 7.12 (m, 2H), 7.30 (t, 1H), 7.38 (d, 1H), 7.56 (m, 4H), 7.70 (m, 2H), 7.91 (d, 2H); M/z (−) 457 (M−H+).

Workup

  1. stirringthe reaction stirred vigorously for 2 hours
  2. extractionextracted with dichloromethane
  3. dry with materialCombined organic extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8426fceb55e3456385e278da5ba5ca1f
Source dataset
uspto-grants-2002_08
Patent number
US06441004B1

Reaction notes

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