Water → HCID 10713360, compound

HRID 2226868Notes

Reaction equation

HRID 2226868 reaction equation
[CH3:1][CH:2]([SH:4])[CH3:3].Cl[C:6]1[C:7]2[CH:17]=[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=[CH:14][C:8]=2[S:9][C:10]=1[C:11]([NH2:13])=[O:12].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.O>CN(C=O)C>[CH3:1][CH:2]([S:4][C:6]1[C:7]2[CH:17]=[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=[CH:14][C:8]=2[S:9][C:10]=1[C:11]([NH2:13])=[O:12])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 63642-PropanethiolHCID 10852993HCID 10852993, compoundHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 10713360HCID 10713360, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

2-Propanethiol (0.8 mL, 8 mmol) is added to a solution of 3-chloro-5-(phenylmethoxy)benzo[b]thiophene-2-carboxamide (1.0 g, 3 mmol) and diazabicycloundecene (DBU) (2.6 mL, 17 mmol) in 10 mL of DMF and the mixture is warmed to 55° C. for 1 hour. The reaction mixture is allowed to cool and then poured into water and stirred. After 1 hour, the precipitate is filtered off, washed with water, and dried to provide 3-[(1-methylethyl)thio]-5-(phenylmethoxy)benzo[b]thiophene-2-carboxamide in 98% yield; mp=150°-152° C.

Workup

  1. temperatureto cool
  2. filtrationthe precipitate is filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-e1e3428240bf4eeb944d9a35c6b0a217
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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