Formaldehyde → HCID 9934084, compound

HRID 1244245Notes

Reaction equation

HRID 1244245 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:14][S:15]([C:18]2[S:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[CH:21][CH:22]=2)(=[O:17])=[O:16])=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[CH:13]=1.[CH2:30](N(CC)CC)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[C:4]([NH:14][S:15]([C:18]2[S:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[CH:21][CH:22]=2)(=[O:16])=[O:17])=[CH:5][C:6]2[CH2:12][CH2:11][N:10]([CH3:30])[CH2:9][CH2:8][C:7]=2[CH:13]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58613358HCID 58613358, compound

Product 1

HCID 9934084HCID 9934084, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of the amine hydrochloride salt D9 (0.96 g, 0.00198 moles) in 1,2-dichloroethane (50 ml) at room temperature was added triethylamine (5 ml, excess) followed by 37% aqueous formaldehyde (5 ml, excess). After vigorous stirring for 5 minutes, sodium triacetoxyborohydride (5 g, excess) was added portionwise over 5 minutes and the resultant solution stirred for a further 2 hours. The reaction was partitioned between water and dichloromethane and the organic phase washed with water, brine and dried over anhydrous MgSO4. The solution was evaporated to dryness affording the title compound E1 as a pale yellow solid (0.993 g, 100%). M-H 461. 1H NMR: δ CDCl3 2.67–2.88 (6H, m), 3.60–3.95 (8H, m), 6.58 (1H, s), 7.07 (1H, S), 7.13 (1H, d), 7.33–7.50 (6H, m).

Workup

  1. customThe reaction was partitioned between water and dichloromethane
  2. washthe organic phase washed with water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-16bd1f3da68643d1b29743bd5cd88952
Source dataset
uspto-grants-2006_10
Patent number
US07122538B2

Reaction notes

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