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2-Furanmethanaminium, N,N,N-trimethyl-, iodide (1:1) → HCID 21520115, compound

HRID 1282792
Notes
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Reaction equation

HRID 1282792 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[I-].C[N+](C)(C)[CH2:31][C:32]1[O:36][CH:35]=[CH:34][CH:33]=1.[OH-].[Na+]>C(OCCOCCOCC)C>[O:36]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH2:31][S:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 109372-Furanmethanaminium, N,N,N-trimethyl-, iodide (1:1)HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 21520079HCID 21520079, compound

Product 1

HCID 21520115HCID 21520115, compound

Reagents, catalysts & solvents 1

HCID 8179
Diethylene glycol diethyl ether
Solvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-mercapto-4-phenoxy-5-sulfamylbenzoic acid (1.6 g) in diethylene glycol diethyl ether (15 ml), anhydrous potassium carbonate (0.5 g) and trimethylfurfurylammonium iodide (2 g) were added. The resulting mixture is stirred at 110°C. for 4 hours, cooled and poured into 0.3 N sodium hydroxide (75 ml). After extraction twice with diethyl ether, the aqueous layer is adjusted to pH 3 by addition of acetic acid. The reaction product is extracted with ethyl acetate, and the resulting organic solution is evaporated in vacuo. The residue is triturated with aqueous acetone giving rise to crystallisation. The 3-(2-furylmethylthio)-4-phenoxy-5-sulfamylbenzoic acid thus obtained is recrystallized from aqueous ethanol and dried. The compound is obtained with a melting point of 214°-216°C.

Workup

  1. temperaturecooled
  2. extractionAfter extraction twice with diethyl ether
  3. additionthe aqueous layer is adjusted to pH 3 by addition of acetic acid
  4. extractionThe reaction product is extracted with ethyl acetate
  5. customthe resulting organic solution is evaporated in vacuo
  6. customThe residue is triturated with aqueous acetone giving rise to crystallisation

Sources & evidence

ORD record
ord-feedc16270024ab79d3caeb56f5b3a20
Source dataset
uspto-grants-1976_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03972886

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes