Phosphorus oxychloride → 3-(Butylamino)-5-cyano-2-phenoxybenzene-1-sulfonamide

HRID 2082889Notes

Reaction equation

HRID 2082889 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([NH2:11])=O)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)=O>>[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:9]#[N:11])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 215060653-Butylamino-4-phenoxy-5-sulphamyl-benzamide

Product 1

HCID 538981403-(Butylamino)-5-cyano-2-phenoxybenzene-1-sulfonamide

Conditions

Temperature
120 °C

Procedure

A mixture of 3-n-butylamino-4-phenoxy-5-sulfamylbenzamide (8.5g) and phosphorus oxychloride (25 ml) is heated at 120° C. for 2 hours. The mixture is then evaporated in vacuo and the residue is triturated with icewater (120 ml) to yield crude 3-n-butylamino-4-phenoxy5-sulfamylbenzonitrile. After filtration, carefully washing with water, drying and recrystallization from methanol, it is obtained with a melting point of 217°-218° C.

Workup

  1. customThe mixture is then evaporated in vacuo
  2. customthe residue is triturated with icewater (120 ml)

Sources & evidence

ORD record
ord-9bcba19fbc9846c8a84e47d7bcfc1158
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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