Hydrochloric Acid → 1-(2-Hydroxymethylbenzoyl)-2-methyl-4-(3-fluorophenyl)-3-thiosemicarbazide

HRID 893880Notes

Reaction equation

HRID 893880 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[C:7]([NH:9][N:10]([CH3:21])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)=[S:12])=[O:8])(OC)=[O:2].[BH4-].[Na+].O.Cl>C(O)C>[OH:2][CH2:1][C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[C:7]([NH:9][N:10]([CH3:21])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)=[S:12])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 133374921-(2-Carbomethoxybenzoyl)-2-methyl-4-(3-fluorophenyl)-3-thiosemicarbazide

Product 1

HCID 133374931-(2-Hydroxymethylbenzoyl)-2-methyl-4-(3-fluorophenyl)-3-thiosemicarbazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-Carbomethoxybenzoyl)-2-methyl-4-(3-fluorophenyl)-3-thiosemicarbazide (7.2 g) was dissolved in ethanol (100 ml). The solution was cooled to below 10° and sodium borohydride (1.1 g) added. The mixture was then stirred at room temperature for 60 hours. Water was then added with production of an amorphous precipitate. Dilute hydrochloric acid was then added to the filtrate to bring it to pH 7 and further precipitate removed by filtration. The filtrate was thereupon acidified to yield the title product as a solid, m.p. 136°-137°, yield 3.4 g.

Workup

  1. temperatureThe solution was cooled to below 10°
  2. customremoved by filtration

Sources & evidence

ORD record
ord-78483baa3c354e2180f91f763a0033ea
Source dataset
uspto-grants-1981_08
Patent number
US04282031

Reaction notes

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