Water → HCID 21484312, compound

HRID 1415304Notes

Reaction equation

HRID 1415304 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][C:7](=[S:9])[S-:8])=[CH:4][CH:3]=1.[CH2:12]([NH+](CC)CC)C.C(Br)Br.C(N(CC)CC)C.O>CN(C)C=O.CO>[OH:1][C:2]1[CH:11]=[CH:10][C:5]([N:6]=[C:7]2[S:8][CH2:12][S:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3024DibromomethaneHCID 8471TriethylamineHCID 13635466162812-90-2

Product 1

HCID 21484312HCID 21484312, compoundYield 24.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of triethylammonium 4-hydroxydithiocarbanilate (28.6 g) in dimethylformamide (100 ml) is added to a mixture of methylene bromide (52.2 g), triethylamine (10.1 g) and dimethylformamide (200 ml) over a 15-minute period while the temperature is being kept below 30° C. The mixture is stirred overnight, poured into water and the aqueous mixture extracted with benzene. The benzene solution is washed, dried, and stripped to yield 12.5 g (63.5% of theory) crude product, as a brown solid. The crude product is dissolved in hot methanol (100 ml) and the solution allowed to stand in the cold one day to yield 4.9 g of a bone-white solid, melting point 162° C to 163° C.

Workup

  1. customis being kept below 30° C
  2. extractionthe aqueous mixture extracted with benzene
  3. washThe benzene solution is washed
  4. customdried
  5. customto yield 12.5 g (63.5% of theory) crude product
  6. customto stand in the cold one day

Sources & evidence

ORD record
ord-eab8b58c42354662a6bc2d4b694fffb2
Source dataset
uspto-grants-1977_01
Patent number
US04004019

Reaction notes

Loading…