Hydrogen Sulfide → Thiobenzamide

HRID 1657084Notes

Reaction equation

HRID 1657084 reaction equation
CC([C:5]1[CH:6]=[C:7]([CH:10]=[C:11](C(C)(C)C)[C:12]=1OCOCCOC)[C:8]#[N:9])(C)C.C(N(CC)CC)C.N1C=CC=CC=1.[SH2:37]>>[C:7]1([C:8](=[S:37])[NH2:9])[CH:10]=[CH:11][CH:12]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 8471TriethylamineHCID 100416433,5-Bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]benzonitrile

Product 1

HCID 683563Thiobenzamide

Procedure

Into a solution containing 10.0 g (0.03 mole) of 3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]-benzonitrile, 5.7 ml (0.04 mole) of triethylamine and 14.2 ml (0.18 mole) of pyridine, hydrogen sulfide gas is bubbled over 15 hours. The mixture is poured into ice water (110 ml), and an oily precipitate solidifies upon standing at 0° C. for 15 hours. The solid is thoroughly washed with water and filtered. Recrystallization from ethyl acetate and hexane gives 7.9 g (71%) of analytically pure 3,5-bis(1,1-dimethylethyl)-4-[2-methoxyethoxy)methoxy]benzenecarbothioamide, mp 113°-115° C.

Workup

  1. customis bubbled over 15 hours
  2. additionThe mixture is poured into ice water (110 ml)
  3. washThe solid is thoroughly washed with water
  4. filtrationfiltered
  5. customRecrystallization from ethyl acetate and hexane

Sources & evidence

ORD record
ord-4e19065f457344129d5ea77903fef6c1
Source dataset
uspto-grants-1993_10
Patent number
US05256680

Reaction notes

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