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

HRID 1605523
Notes
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Reaction equation

HRID 1605523 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-d67c2457057a4adb895b7e713365ef3d
Source dataset
uspto-grants-1976_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03950376

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes