Phosgene → HCID 70514272, compound

HRID 1648834Notes

Reaction equation

HRID 1648834 reaction equation
[C:1]([NH:4]/[CH:5]=[CH:6]\[S:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[CH3:2].CN1CCOCC1.C(Cl)(Cl)=O.[N-:38]=[N+:39]=[N-:40].CN(C)C(=[NH2+])N(C)C>ClCCl.C1(C)C=CC=CC=1.[Cl-].[Na+].O.O>[CH3:2][C:1]1[N:4](/[CH:5]=[CH:6]\[S:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:40]=[N:39][N:38]=1

Participants

9

Reactant 4

HCID 6371PhosgeneHCID 79724-MethylmorpholineHCID 12620558HCID 12620558, compoundHCID 178484365HCID 178484365, compound2×

Product 1

HCID 70514272HCID 70514272, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

(Z)-1-Acetamido-2-triphenylmethylthioethene, e44, (1.07 g) in dry dichloromethane (30 ml) containing N-methylmorpholine (3.5 ml, 3.22 g) was cooled to -30° and treated with phosgene in toluene (8.4 ml, 12.5% w/w). After warming to room temperature and stirring for 30 minutes tetramethylguanidinium azide (600 mg) in dichloromethane (6 ml) was added. After 45 min. a further quantity of tetramethylguanidinium azide (300 mg) in dichloromethane was added. After a further 45 min. the reaction mixture was warmed with water (2×300 ml), followed by saturated brine. After drying (MgSO4) the dichloromethane was evaporated in vacuo. Toluene (30 ml) was added and evaporated in vacuo (2×) and the residual material was crystallised from ethyl acetate/hexane to give (Z)-1-(5-methyltetrazol-1-yl)-2-triphenylmethylthioethene (827 mg), m.p. 208°-210°, νmax. (CHCl3) 1600, 1490, 1445, 1410 cm-1, δ(CDCl3) 2.54 (3H, s), 6.15 (1H, d, J 9 Hz), 6.59 (1H, d, J 9 Hz), 7.35 (15 H, s) p.p.m. (Found: C, 71.65; H, 5.20; N, 14.41%. C23H20N4S requires C, 71.9; H, 5.21; N, 14.6%).

Workup

  1. temperaturewas cooled to -30°
  2. additionwas added
  3. dry with materialAfter drying (MgSO4) the dichloromethane
  4. customwas evaporated in vacuo
  5. additionToluene (30 ml) was added
  6. customevaporated in vacuo (2×)
  7. customthe residual material was crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-078c67dcae9e44f0aac71e6862dfc71d
Source dataset
uspto-grants-1983_11
Patent number
US04413000

Reaction notes

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