O-Phenylenediamine → HCID 53354006, compound

HRID 1926219Notes

Reaction equation

HRID 1926219 reaction equation
[CH:1]1[C:14]2[C:13](=[CH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=O)=[O:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.O[C:40]1[C:48]2[N:47]=N[NH:45][C:44]=2[CH:43]=[CH:42][CH:41]=1.C(N(CC)CC)C.C1(N)C=CC=CC=1N>[Cl-].[Na+].O.CN(C=O)C>[CH:1]1[C:14]2[C:13](=[CH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([NH:45][C:44]3[CH:43]=[CH:42][CH:41]=[CH:40][C:48]=3[NH2:47])=[O:26])=[O:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57972064HCID 57972064, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 53354006HCID 53354006, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-(2-(9H-thioxanthen-9-ylidene)acetamido)hexanoic acid (367 mg, 1 mmol), and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodi-imide hydrochloride (394 mg, 2 mmol), hydroxy-benzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and o-phenylenediamine (432 mg, 4 mmol) were added. The mixture was stirred for 24 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (302 mg, 66% yield) as a brown solid. LC-MS (m/z) 458 (M+1).

Workup

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4bcefecf6bb842cc9198f270717b0e26
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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