O-Phenylenediamine → HCID 53354005, compound

HRID 1926216Notes

Reaction equation

HRID 1926216 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)[O: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:11]1[C:12]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:14]3[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=3)[O:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57972060HCID 57972060, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 53354005HCID 53354005, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-(2-(9H-xanthen-9-ylidene)acetamido)hexanoic acid (351 mg, 1 mmol), and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide 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 (335 mg, 76% yield) as a brown solid. LC-MS (m/z) 442 (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-d9395a66edfa42439f84a2e8cb2fbef1
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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