Ammonia → HCID 15315497, compound

HRID 1153866Notes

Reaction equation

HRID 1153866 reaction equation
[NH3:1].[Br:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11].BrCC1C=CC(S(Cl)(=O)=O)=CC=1>O1CCCC1>[Br:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH2:1])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86739782HCID 86739782, compound

Product 1

HCID 15315497HCID 15315497, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ammonia (1.0 ml) in tetrahydrofuran (50 ml) at -78° was contacted dropwise with a solution of a 60/40 mixture of 2-(bromomethyl)benzenesulfonyl chloride/4-(bromomethyl)benzenesulfonyl chloride (4.52 g) in tetrahydrofuran (20 ml). The stirred mixture was allowed to warm to 0° and volatiles were removed in vacuo. The residue was contacted with water (50 ml) and extracted three times with ethyl acetate. Combined organic portions were washed with brine, dried, and evaporated to give 4.00 g of white solid. 1H nmr δ(CD3)2COTMS 8.15-7.20 (m), 6.7-6.3 (m, NH), 4.95 (q, area 21), 4.55 (s, area 18), consistent with a ca. 60/40 mixture of 2-(bromomethyl)-/4-(bromomethyl)-benzenesulfonamides. The sample was fractionally recrystallized from chloroform, but without significant change in isomeric content.

Workup

  1. temperatureto warm to 0°
  2. customvolatiles were removed in vacuo
  3. extractionextracted three times with ethyl acetate
  4. washCombined organic portions were washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-d3e317d2721a4f0998e66847896743d3
Source dataset
uspto-grants-1984_12
Patent number
US04486589

Reaction notes

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