Sodium hydride → HCID 178514759, compound

HRID 2414132Notes

Reaction equation

HRID 2414132 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([SH:8])[CH2:4][CH2:3]1.[H-].[Na+].CN(C)C=[N:14][S:15]([C:18]1[S:19][C:20](Br)=[CH:21][CH:22]=1)(=[O:17])=[O:16]>CN(C=O)C>[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([S:8][C:20]2[S:19][C:18]([S:15]([NH2:14])(=[O:17])=[O:16])=[CH:22][CH:21]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 54319951N,N-Dimethyl-N'-(5-bromothiophene-2-sulfonyl)formamidineHCID 178521616HCID 178521616, compound

Product 1

HCID 178514759HCID 178514759, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Trans-4-Hydroxycyclohexylmercaptan (9.92 g, 0.075 mol) in DMF (10 ml) was added dropwise to a stirred mixture of NaH (3.45 g, 50 % oil, 0.075 mol) and DMF (40 ml). When gas evolution was complete, N,N-dimethyl-N'-(5-bromothiophene-2-sulfonyl)formamidine (14.85 g, 0.05 mol) was added in one portion, rinsed in with DMF (10 ml) and the resulting mixture was heated on the steam bath for 1 hour. The DMF was removed under reduced pressure and the residue was stirred with methanol (50 ml) and 10% sodium hydroxide solution (50 ml) overnight. The methanol was evaporated and the resulting aqueous solution was added to 10% HCl (400 ml) and chilled. The solid that separated was collected and washed with water. The residue was triturated with 1-chlorobutane to give a solid, (12.0 g) after drying. Recrystallization from water followed by dichloroethane gave material with m.p. 145°-147° C.

Workup

  1. washrinsed in with DMF (10 ml)
  2. temperaturethe resulting mixture was heated on the steam bath for 1 hour
  3. customThe DMF was removed under reduced pressure
  4. customThe methanol was evaporated
  5. additionthe resulting aqueous solution was added to 10% HCl (400 ml)
  6. temperaturechilled
  7. customThe solid that separated
  8. customwas collected
  9. washwashed with water
  10. customThe residue was triturated with 1-chlorobutane
  11. customto give a solid, (12.0 g)
  12. customafter drying
  13. customRecrystallization from water
  14. customgave material with m.p. 145°-147° C.

Sources & evidence

ORD record
ord-7b0471f020e44fcebd9d52f24f87c482
Source dataset
uspto-grants-1988_01
Patent number
US04721794

Reaction notes

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