Methanol → HCID 178527935, compound

HRID 1157135Notes

Reaction equation

HRID 1157135 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([NH:12][NH2:13])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[K+].CO.[C:18](=S)=[S:19]>O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:18]([SH:19])=[N:13][N:12]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6348Carbon Disulfide2×HCID 14797Potassium HydroxideHCID 891583,4-Methylenedioxybenzoic acid hydrazide

Product 1

HCID 178527935HCID 178527935, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzo[1,3]dioxole-5-carboxylic acid hydrazide (45.8 g, 254 mmol) was added to a mixture of potassium hydroxide (15.7 g, 280 mmol) and methanol (350 ml). The mixture was stirred for 30 minutes at room temperature. Carbon disulfide (38.7 g, 508 mmol) was added. The mixture was stirred at reflux for 20 hours, followed by another portion of carbon disulfide (12.7 g, 167 mmol) and reflux for 4 h. Water (300 ml) was added and the excess of carbon disulfide and methanol was evaporated. The aqueous suspension was acidified by adding concentrated hydrochloric acid to pH 3-4. The product precipitated, filtered and was washed with water (50 ml). Yield 53.5 g (95%) as yellow powder.

Workup

  1. stirringThe mixture was stirred
  2. temperatureat reflux for 20 hours
  3. temperaturereflux for 4 h
  4. customthe excess of carbon disulfide and methanol was evaporated
  5. additionby adding concentrated hydrochloric acid to pH 3-4
  6. customThe product precipitated
  7. filtrationfiltered
  8. washwas washed with water (50 ml)

Sources & evidence

ORD record
ord-73df3b30816d4168bbb87b478c1fea08
Source dataset
uspto-grants-2010_10
Patent number
US07807667B2

Reaction notes

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