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Hydrochloric Acid → HCID 20033680, compound

HRID 231682
Notes
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Reaction equation

HRID 231682 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[S:19][C:18]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)=O.Cl.[CH2:26](NCCC1C=CC(S(C2SC(S(N)(=O)=O)=CC=2)(=O)=O)=CC=1)[CH3:27].CN(C)CCCC1C=CC(S(C2SC(S(N)(=O)=O)=CC=2)(=O)=O)=CC=1.CN(C)CCCCC1C=CC(S(C2SC(S(N)(=O)=O)=CC=2)(=O)=O)=CC=1>O1CCCC1>[CH3:1][N:2]([CH3:24])[CH:3]([CH2:26][CH3:27])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[S:19][C:18]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 20033708HCID 20033708, compoundHCID 20033710HCID 20033710, compoundHCID 20033716HCID 20033716, compoundHCID 20033728HCID 20033728, compound

Product 1

HCID 20033680HCID 20033680, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-(4-dimethylcarbamoylmethylphenylsulfonyl)thiophene-2-sulfonamide (1.35 g) was dissolved in 30 ml of tetrahydrofuran under a nitrogen atmosphere. Borane tetrahydrofuran complex (8 ml of 1 molar solution) was added and the mixture was stirred at room temperature for 3 hours. Hydrochloric acid (20 ml of 6N) was then added cautiously and the mixture was heated on a steam bath, boiling off tetrahydrofuran. The acidic solution was cooled to room temperature and extracted with chloroform. The aqueous phase was separated and its pH adjusted to pH 8.5 before extracting it with ethyl acetate. The ethyl acetate phase was dried over sodium sulfate and concentrated under vacuum to give a residue of an oily solid. This was chromatographed on silica gel to give a pure product, m.p. 169°-172° C. N.M.R. (DMSO, d6) δ: 2.17 (6H, s), 2.50 (2H, T, J=6 Hz), 2.82 (2H, T, J=6 Hz), 7.55 (2H, d, J=9 Hz), 7.60 (1H, d, J=4 Hz), 7.87 (1H, d, J=4 Hz), 7.94 (2H, d, J=9 Hz), 8.04 (2H, broad s). Anal Calc'd for C14H18N2O4S3 : C, 44.90; H, 4.84; N, 7.48. Found: C, 44.54; H, 4.89; N, 7.60. The following compounds where also made by similar procedures: 5-[4-(2-ethylaminoethyl)phenylsulfonyl]thiophene-2-sulfonamide (m.p. 174-177). 5-[4-(3-methylaminopropyl)phenylsulfonyl]thiophene-2-sulfonmide (m.p. 178°-179.5° C.), 5-[4-(3-dimethylaminopropyl)phenylsulfonyl]thiophene-2-sulfonamide (m.p. 163°-164.5° C.), and 5-[4-(4-dimethylaminobutyl)phenylsulfonyl]thiophene-2-sulfonamide (m.p. 186°-189° C.).

Workup

  1. additionBorane tetrahydrofuran complex (8 ml of 1 molar solution) was added
  2. temperaturethe mixture was heated on a steam bath
  3. temperatureThe acidic solution was cooled to room temperature
  4. extractionextracted with chloroform
  5. customThe aqueous phase was separated
  6. extractionbefore extracting it with ethyl acetate
  7. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customto give a residue of an oily solid
  10. customThis was chromatographed on silica gel
  11. customto give a pure product, m.p. 169°-172° C

Sources & evidence

ORD record
ord-cafc0eb136e247d58e5a51f3ab7293c1
Source dataset
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04847289

Reaction notes

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