(Furan-2-yl)-N,N,N-trimethylmethanaminium iodide → HCID 21520115, compound

HRID 1605523Notes

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]

Participants

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

temperaturecooled
extractionAfter extraction twice with diethyl ether
additionthe aqueous layer is adjusted to pH 3 by addition of acetic acid
extractionThe reaction product is extracted with ethyl acetate
customthe resulting organic solution is evaporated in vacuo
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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