Dimethylformamide → HCID 15077501, compound

HRID 1074205Notes

Reaction equation

HRID 1074205 reaction equation
[SH:1][C:2]1[N:3]([CH3:7])[CH:4]=[CH:5][N:6]=1.[H-].[Na+].CN(C)C=O.Cl[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[N+:24]([O-:26])=[O:25]>C(O)(=O)C>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([S:1][C:2]2[N:3]([CH3:7])[CH:4]=[CH:5][N:6]=2)=[C:17]([N+:24]([O-:26])=[O:25])[CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 251404-Chloro-3-nitroanisoleHCID 178480602HCID 178480602, compound

Product 1

HCID 15077501HCID 15077501, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2-mercapto-1-methylimidazole (1.14 g, 10 mmoles), 0.6 of 60% sodium hydride in mineral oil and 20 ml of N,N-dimethylformamide was added 1.88 g (10 mmoles) of 4-chloro-3-nitroanisole. The mixture was stirred at room temperature for 0.5 hours and then heated at 90°-100° C. for 4 hours. After cooling in an icebath, 0.5 ml of acetic acid was added and the mixture was partitioned between dichloromethane and dilute sodium bicarbonate. The organics were concentrated on a steam bath to a small volume and the residue was chromatographed on silica gel using ethyl acetate as the eluent. The fractions containing the product were combined and concentrated to give 1.0 g (38%) of the product, mp 117°-120° C.).

Workup

  1. temperatureheated at 90°-100° C. for 4 hours
  2. additionwas added
  3. customthe mixture was partitioned between dichloromethane and dilute sodium bicarbonate
  4. concentrationThe organics were concentrated on a steam bath to a small volume
  5. customthe residue was chromatographed on silica gel
  6. additionThe fractions containing the product
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c2c65d00b2024896aa4b9630fa0b820d
Source dataset
uspto-grants-1990_11
Patent number
US04973599

Reaction notes

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